Category: 110661-91-1

Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 110661-91-1, Formula: C8H15BrO2

a) A mixture of 3-chloro-4-hydroxy-5-methyl-benzonitrile (1 .15 g, 6.87 mmol) and Cs2C03 (13.43 g, 41.2 mmol) in DMF (45 ml.) is stirred at rt for 30 min before tert.-butyl 4- bromobutanoate (1 .55 g, 6.95 mmol) is added. The orange suspension is stirred at 65C for 72 h. Another portion of tert.-butyl 4-bromobutanoate (1 .55 g, 6.95 mmol) is added and stirring is continued at 65C for 24 h. The mixture is dilued with water (150 ml.) and extracted three times with DCM (3×50 ml.) and EA (3×50 ml_). The org. extracts are combined, dried over MgS04, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:EA:methanol to give tert-butyl 4-(2-chloro-4-cyano- 6-methylphenoxy)butanoate (645 mg) as a colourless oil; LC-MS: tR = 1 .01 min, [M+H]+ = no mass detectable; 1 H NMR (D6-DMSO): delta 7.94 (d, J = 1 .7 Hz, 1 H), 7.75 (d, J = 1.3 Hz, 1 H), 3.95 (t, J = 6.3 Hz, 2 H), 2.46 (t, J = 7.2 Hz, 2 H), 2.30 (s, 3 H), 1.98 (quint, J = 6.6 Hz, 2 H), 1 .41 (s, 9 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; LESCOP, Cyrille; MATHYS, Boris; MORRISON, Keith; MUELLER, Claus; NAYLER, Oliver; STEINER, Beat; WO2012/98505; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 110661-91-1,Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Part A Preparation of 6-[(5-Hydroxypentyl)oxy]-2-(4-t-butoxy-4-oxobutyloxy)benzenepropanoic Acid Methyl Ester A mixture of 2-hydroxy-6-[(5-hydroxypentyl)oxy]-benzenepropanoic acid methyl ester (2.04 g, 7.23 mmol) (as described by Cohen, N. EP Appl. 531,823), t-butyl 4-bromobutyrate (1.93 g, 8.67 mmol), and K2CO3 (2.29 g, 16.6 mmol) in DMSO (60 mL) was stirred at ambient temperatures under nitrogen for 21 h. The solids were removed by filtration and the filtrate was diluted with water (100 mL), and extracted with EtOAc (3*100 mL). The combined organic extracts were washed with water and sat. NaCl, dried (MgSO4), and concentrated to give product as a yellow oil (2.98 g). A portion (487 mg) was purified by silica gel flash chromatography (40:60 EtOAc/hexanes) to give the title compound as a colorless oil (367 mg, 73.3%). 1H NMR (CDCl3): 7.08 (t, J=8.2 Hz, 1H), 6.48 (d, J=8.2 Hz, 2H), 4.00-3.89 (m, 4H), 3.70-3.62 (m, 5H), 3.04-2.93 (m, 2H), 2.50-2.39 (m, 4H), 2.11-1.99 (m, 2H), 1.88-1.75 (m, 2H), 1.72-1.52 (m, 5H), 1.43 (s, 9H); MS: m/e 447.3 [M+Na].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-bromobutanoate, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; US6416733; (2002); B1;; ; Patent; Carpenter JR., Alan P.; US2003/3049; (2003); A1;; ; Patent; Barrett, John Andrew; Cheesman, Edward Hollister; Harris, Thomas David; Liu, Shuang; Rajopadhye, Milind; Sworin, Michael; US2003/124053; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: tert-Butyl 4-bromobutanoate

Intermediate 6 (10.47 g, 11.73 mmol) was dissolved in acetonitrile (500 ml) and tert-butyl bromoacetate (10.0 g, 44.84 mmol) and DIPEA (9.08 mg, 70.38 mmol) were added. The reaction mixture was stirred at RT for 14 days and then filtered. Evaporation of the solvent gave crude product which was purified using a Combiflash companion (120 g cartridge) eluting with 0-10% MeOH in DCM. The solid product was triturated with Et2O to give a white solid. Yield: 8.79 g (72%) LC-MS (Method 2): Rt = 2.93 min, m/z = 1036 [M+H]+

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2009/60206; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 110661-91-1

General procedure: To 100 mLrbf was added a mixture of compound 20 (1.66 g, 10 mmol), cesiumcarbonate (3.26 g, 10 mmol), TBAI (3.70 g, 10 mmol) and anhydrousDMF (20 mL). Compound 19 (2.23 g, 10 mmol) was added dropwise tothe mixture. The reaction mixture was then stirred at room temperaturefor 3 h. Ethyl acetate was added into the reaction mixture. The combinedmixture was washed with two portions of water. After evaporationof the solvent under reduced pressure MeOH (20 mL) was addedfollowed by silica gel (1 g). The resulting plug was loaded on to a silicagel column and eluted with 1:10 (ethyl acetate: hexane). Fractions withand Rf = 0.64 (hexane:ethyl acetate 1:1) were pooled and evaporatedto afford tert-butyl esters (1.47 g, yield; 47%). Trifluoroacetic acid wasthen added into the tert-butyl esters and mixture was stirred at roomtemperature for 30 min. Excess of trifluoroacetic acid was evaporatedand MeOH (20 mL) was added followed by silica gel (1 g). The resultingplug was loaded on to a silica gel column and eluted with 1:10 (ethylacetate: hexane). Fractions with and Rf = 0.45 (TLC) (Hexane: ethylacetate,1:1) were pooled and evaporated to afford 22 (1 g, yield 83%)as white solid.

The synthetic route of tert-Butyl 4-bromobutanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dekhne, Aamod S.; Gangjee, Aleem; Golani, Lalit K.; Hou, Zhanjun; Islam, Farhana; Matherly, Larry H.; O’Connor, Carrie; Bioorganic and medicinal chemistry; vol. 28; 12; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 110661-91-1, Safety of tert-Butyl 4-bromobutanoate

a) A mixture of 3-chloro-4-hydroxy-5-methyl-benzonitrile (1.15 g, 6.87 mmol) and Cs2CO3 (13.43 g, 41.2 mmol) in DMF (45 mL) is stirred at rt for 30 min before tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added. The orange suspension is stirred at 65 C. for 72 h. Another portion of tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added and stirring is continued at 65 C. for 24 h. The mixture is dilued with water (150 mL) and extracted three times with DCM (3*50 mL) and EA (3*50 mL). The org. extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:EA:methanol to give tert-butyl 4-(2-chloro-4-cyano-6-methylphenoxy)butanoate (645 mg) as a colourless oil; LC-MS: tR=1.01 min, [M+H]+=no mass detectable; 1H NMR (D6-DMSO): delta 7.94 (d, J=1.7 Hz, 1H), 7.75 (d, J=1.3 Hz, 1H), 3.95 (t, J=6.3 Hz, 2H), 2.46 (t, J=7.2 Hz, 2H), 2.30 (s, 3H), 1.98 (quint, J=6.6 Hz, 2H), 1.41 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Morrison, Keith; Mueller, Claus; Nayler, Oliver; Steiner, Beat; US2013/303514; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110661-91-1, A common compound: 110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of 3-mercapto-5-trifluoromethyl-benzoic acid methyl ester (990 mg, 4.19 mmol) in acetonitrile (25 mL) were added N,N-diisopropylethylamine (1.08 g, 1.46 mL, 8.38 mmol) and tert-butyl 4-bromobutanoate (935 mg, 4.19 mmol, CAS RN 110611-91-1). The clear yellow solution was stirred at room temperature for 2.5 hours and then poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 50 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow liquid (1.27 g, 80%). MS (ESI+): m/z=379 ([M+]).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl 4-bromobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Dehmlow, Henrietta; Erickson, Shawn David; Mattei, Patrizio; Richter, Hans; US2013/267519; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110661-91-1, These common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2: Preparation of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate A flask was charged with 2-hydroxy-4-(trifluoromethyl)benzaldehyde (300 mg, 1.58 mmol, 1.00 equiv), DMF (10 mL), potassium carbonate (654 mg, 4.73 mmol, 3.00 equiv), and tert-butyl 4-bromobutanoate (702 mg, 3.15 mmol, 2.00 equiv). The resulting solution was stirred overnight at 100 C. and quenched with water (30 mL). The resulting solution was extracted with DCM (2*50 mL) and the organic layers were combined, washed with brine (2*30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was chromatographed on a silica gel column with EtOAc/petroleum ether (1/10) to provide 450 mg (86% yield) of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate as a light yellow solid. 1H NMR (300 MHz, Chloroform-d) delta 10.5 (s, 1H), 7.96 (d, J=7.5 Hz, 1H), 7.29-7.33 (m, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.50 (t, J=6.0 Hz, 2H), 2.18-2.25 (m, 2H), 1.49 (s, 9H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 110661-91-1.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; (108 pag.)US2018/134674; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110661-91-1, A common compound: 110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Exemplification of General Procedure J:; Preparation of tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)- lH-indol-l-yl)butanoate; To a solution of 3-(3-chloro-4-isopropoxyphenyl)-5-(lH-indol-4-yl)-l,2,4-oxadiazole (0.100 g, 0.283 mmol) in DMF (0.999 ml) was added NaH (0.012 g, 0.311 mmol). After about 15 min tert-butyl 4-bromobutanoate (0.095 g, 0.424 mmol) was added and the reaction mixture was heated to about 500C. After about 24h the reaction mixture was cooled to ambient temperature, concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5- yl)-lH-indol-l-yl)butanoate (0.135 g, 93%) as a colorless oil that solidified on standing. LCMS (Table 1, Method c) Rt = 3.50 min, m/z 496 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl 4-bromobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/76356; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 110661-91-1, 110661-91-1

To a solution of ethyl 2-(piperazin-1-yl)pyrimidine-5-carboxylate hydrochloride (10 g, 36.67 mmol, 1.0 equiv, HCl) and tert-butyl 4-bromobutanoate (8.18 g, 36.67 mmol, 1.0 equiv) in DMF (100 mL) was added Et3N (15.31 mL, 110.00 mmol, 3.0 equiv). The mixture was stirred at 130 C for 14 h. The mixture was then poured into H2O (400 mL) and the solution was extracted with EtOAc (3 x 150 mL). The combined organic layer was washed with brine (200 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (5/1 to 1/1 petroleum ether/EtOAc) to give the product (9.5 g, 68.5% yield) as a yellow solid. LCMS (ESI) m/z: [M + H] calcd for C19H30N4O4: 379.24; found 379.2, 380.2.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl 4-bromobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; REVOLUTION MEDICINES, INC.; PITZEN, Jennifer; GLIEDT, Micah James Evans; BURNETT, G. Leslie; AGGEN, James Bradley; KISS, Gert; CREGG, James Joseph; SEMKO, Christopher Michael; WON, Walter; WANG, Gang; LEE, Julie Chu-Li; THOTTUMKARA, Arun P.; GILL, Adrian Liam; MELLEM, Kevin T.; (484 pag.)WO2019/212990; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 110661-91-1 name is tert-Butyl 4-bromobutanoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 110661-91-1

Methyl 3-(4-(tert-butoxy)-4-oxobutoxy)beiizoate A solution of methyl 3Thydroxybenzoate (commercially available from for example Aldrich) (1 g, 6.6 mmol) and K2C03 (1.82 g, 13.2 mmol) in DMF (10 mL) was treated with tert-butyl 4-bromobutanoate (commercially available from for example Aldrich) (2.2 g, 9.9 mmol) and the mixture was stirred at 60 C for 16 hours. A further aliquot of K2C03 (1.82 g, 13.2 mmol) and tert-butyl 4-bromobutanoate (2.2 g, 9.9 mmol) were added and the mixture was heated at 60 C for further 6 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was washed with brine (2 x 50 mL), dried (hydrophobic frit) and evaporated to dryness. The product was purified by chromatography on silica using a gradient elution from 0% to 100% methyl tert-butyl ether in cyclohexane to afford the title compound (1.4 g, 4.8 mmol, 72 % yield). LCMS RT= 1.26 min, ES+ve m/z 312 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; YALE UNIVERSITY; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMBRIDGE ENTERPRISE LIMITED UNIVERSITY OF CAMBRIDGE; CREWS, Craig, M.; BUCKLEY, Dennis; CIULLI, Alessio; JORGENSEN, William; GAREISS, Peter, C.; MOLLE, Inge, Van; GUSTAFSON, Jeffrey; TAE, Hyun-Seop; MICHEL, Julien; HOYER, Dentin, Wade; ROTH, Anke, G.; HARLING, John, David; SMITH, Ian Edward, David; MIAH, Afjal, Hussain; CAMPOS, Sebastian, Andre; LE, Joelle; WO2013/106646; (2013); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics