Category: 144267-96-9

Reference of 144267-96-9,Some common heterocyclic compound, 144267-96-9, name is Ethyl 3,4-difluorobenzoate, molecular formula is C9H8F2O2, 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.

Following general procedure A, to 4-butylphenol (1.75 mL, 11.4 mmol) and K2CO3 [1-90 g, 13.8 mmol) in DMSO (18 mL) was added ethyl 3,4-difluorobenzoate (1.37 mL, 9 mmol) and the reaction was then stirred at 80 C for 24 hours in an argon atmosphere. The reaction was cooled to room temperature and quenched by the addition of water. The aqueous layer was extracted with EtOAc (3x). The combined organics were washed first with 1 M aqueous NaOH (1x) then washed with brine (1x), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 100% to 80% PE-DCM gradient to give the title compound as colorless oil (1.80 g, 63%).1H NMR (300 MHz, CDCI3) delta 7.84 (dd,j = 11.2, 2.0 Hz, 1H), 7.75 (ddd,/ = 8.5, 2.0, 1.2 Hz, 1H), 7.23 – 7.12 (m, 2H), 7.01 – 6.88 (m, 3H), 4.37 (q, / = 7.1 Hz, 2H), 2.67 – 2.55 (m, 2H), 1.68 – 1.52 (m, 2H), 1.46 – 1.23 (m, 5H), 0.94 ft, / = 7.3 Hz, 3H). 13C NMR (75 MHz, CDCI3) delta 165.4 (d, / = 2.6 Hz), 153.7, 153.0 (d,/ = 249.0 Hz), 149.5 (d,j = 11.2 Hz), 139.3, 129.9, 126.4 (d,/ = 3.5 Hz), 126.0 (d,j = 6.3 Hz), 119.0, 119.0 (d,/ = 1.4 Hz), 118.3 (d, J = 19.9 Hz), 61.3, 35.1, 33.8, 22.5, 14.4, 14.1. HRMS (C19H22F03+): expected: 317.1548; found: 317.1549.

The synthetic route of 144267-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REINMUeLLER, Viktoria; (121 pag.)WO2018/154118; (2018); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 144267-96-9, name is Ethyl 3,4-difluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 3,4-difluorobenzoate

The ester required for the preparation of Example 19b was prepared as follows: Ethyl 3-fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(1H-pyrazol-3- ylamino)carbonyl]phenoxy}benzoate; To a suspension of tert-butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1- methylethoxy] benzoyl} amino)-lH-pyrazole-l-carboxylate (587 mg, 1.5 nunol), caesium carbonate (488 mg, 1.5 mmol) in DMA (3 mL) was added ethyl 3,4-difluorobenzoate (279 mg, 1.5 mmol). This mixture was heated at 110C for 16 hours. The reaction mixture was filtered and concentrated in vacuo then the residue chromatographed on silica, eluting with 0- 70% ethyl acetate in hexane, to give the desired compound as a yellow oil (271 mg, 40%) tu NMR (CDC13) : 1.3 (d, 3H), 1.4 (t, 3H), 3.4 (s, 3H), 3.5 (m, 2H), 4.4 (q, 2H), 4.6 (m, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.1 (s, 1H), 7.15 (s, 1H), 7.3 (s, 1H), 7.5 (d, 1H), 7.8 (d, 1H), 7.85 (d, 1H), 9.4 (s, 1H)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/80359; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 144267-96-9, name is Ethyl 3,4-difluorobenzoate, 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. Recommanded Product: Ethyl 3,4-difluorobenzoate

Cesium carbonate (8.3 g, 25.4 mmol) was added to a mixture of 3-hydroxy-5-{[(1S)-2- hydroxy- 1 -methylethyl]o’xy) -N-( I -methyl- lH-pyrazol-3-yl)benzamide (3.7 g, 12.7 mmol) and ethyl-3,4-difluorobenzoate (2.36 g, 12.7 mmol) in dimethylacetamide (60 mL) and the stirred mixture heated at 115C for 3 hours. The mixture was allowed to cool to RT and ethyl acetate (100 mL) added. The mixture was washed with water (5 x 40 mL), brine (40 mL), dried (MgS04), filtered, and reduced in vacuo. The residue was chromatographed on silica, eluting with 50% ethyl acetate in isohexane, to give the desired compound (1.8 g). ?H NMR No. (CDC13): 1.31 (d, 3H), 1.41 (t, 3H), 3.72 (d, 2H), 3.83 (s, 3H), 4:39 (q, 2H), 4.57 (sex, 1H), 6.75 (m, 1H), 6.83 (m, 1H), 7.09 (m, 2H), 7.30 (d, 2H), 7.83 (m, 2H), 8.91 (brs, 1H). m/z 458(M+H)+

The synthetic route of Ethyl 3,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/121110; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 144267-96-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 144267-96-9, name is Ethyl 3,4-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 3,4-difluorobenzoate (1 .5 g) in N,N-dimethylformannide (15 mL) 1 ,2,4-triazole (1 .1 g) and K2CO3 (2.3 g) are added and the mixture is heated at 150 C in a microwave for 30 min. After cooling, water and ethyl acetate are added and the organic layer is dried over MgSO4 and concentrated. The residue is purified by chromatography on silica gel eluting with 0% to 100% ethyl acetate/hexane. The pure ester is dissolved in methanol (30 mL) and 4 M aqueous NaOH solution (3 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is neutralized with 6 M hydrochloric acid, concentrated, and then acidified with 6 M hydrochloric acid, and the precipitate is filtered off washing with a small amount of water and dried by suction to give the acid as a white solid.

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,4-difluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; NOSSE, Bernd; BLUM, Andreas; HECKEL, Armin; HIMMELSBACH, Frank; ASHWEEK, Neil J.; HARRIOTT, Nicole; WO2014/37327; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 144267-96-9, name is Ethyl 3,4-difluorobenzoate, 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 144267-96-9, Quality Control of Ethyl 3,4-difluorobenzoate

Intermediate 513-Fluoro-4-(2-methyl-1 H-imidazol-1 -yl)-benzoic acidTo a solution of ethyl 3,4-difluorobenzoate (1 .5 g) in N,N-dimethylformaide (12 mL) is added 2-methylimidazole (1 .3 g) and K2CO3 (2.2 g) and the mixture is heated at 140 C in a microwave oven for 1 h. After cooling to room temperature, water and ethyl acetate are added and the organic layer is dried (MgS04) and concentrated. The residue is purified by chromatography (ethyl acetate/hexane 0: 1?1 :0). The ester is dissolved in methanol (30 mL) and 4 M aqueous NaOH (3 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is neutralized with 6 M aqueous HCI, concentrated and then acidified with 6 M aqueous HCI. The precipitate is filtered off washing with a small amount of water and dried by suction to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3,4-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; BLUM, Andreas; BREITFELDER, Steffen; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; WELLENZOHN, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/123449; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 144267-96-9, A common heterocyclic compound, 144267-96-9, name is Ethyl 3,4-difluorobenzoate, molecular formula is C9H8F2O2, 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.

A solution of the respective phenol and the benzoate derivative or, respectively, the carboxylic acid derivative of an aromatic 6-membered heterocycle having 1 or 2 N-atoms, as defined in connection with formula (I), or their substituted derivatives in an appropriate solvent, preferably a polar aprotic solvent, most preferably DMSO, and preferably under addition of anhydrous K2C03 , was stirred at a temperature between 80C and 120C depending on the substrate until the limiting reactant was fully converted. The reaction was guenched by addition of water, extracted with organic solvent (preferably Et20, EtOAc and DCM depending on the substrate). The combined organic layers were washed with sat. agueous NaCI solution, dried over Na2S04 and evaporated to dryness under reduced pressure. The crude product was purified by flash column chromatography to give the desired biarylether. (V138) General procedure A: Ethyl 3,4-difluorobenzoate (348 mg, 1.87 mmol, 1.00 eguiv), 4-(tert- butyOphenol (336 mg, 2.24 mmol, 1.20 eguiv) and K2C03 (388 mg, 2.80 mmol, 1.50 eguiv) in DMSO (2 ml_) were stirred at 100 C for 22 h. Purification by column chromatography (EtOAc/petroleum ether 1/40) gave the desired product as colourless oil (451 mg, 1.43 mmol, 76%); HRMS (ESI) m/z calcd. for C19H2203F+ [M+H]+ 317.1547, found: 317.1549; NMR (400 MHz, Chloroform-cO delta 7.85 (dd, J = 11.2, 2.0 Hz, 1H), 7.80 – 7.73 (m, 1H), 7.42 – 7.35 (m, 2H), 7.02 – 6.94 (m, 3H), 4.37 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz, 3H), 1.33 (s, 9H).

The synthetic route of 144267-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); REINMUELLER, Viktoria; ZHU, Jieping; (56 pag.)WO2017/158190; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics