Category: 69038-74-0

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. 69038-74-0, name is tert-Butyl 3-Bromobenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Reference example 22 tert-Butyl 3-allylbenzoate To a solution of isopropylmagnesium bromide (0.76M THF solution, 26ml, 20mmol) in THF (16ml) was dropped at 0C butyllithium (1.59M hexane solution, 25ml, 40mmol), and the mixture was stirred for 15 minutes, followed by stirring for 20 minutes at -78C. Thereto was dropped a solution of tert-butyl 3-bromobenzoate (2.0g, 8.0mmol) in THF (16ml) and the solution was stirred at -78C for 30minutes. Thereto were added aryl bromide (2.8ml, 32mmol) and copper (I)cyanide (1M THF solution, 2.4ml, 2.4mmol) and the mixture was stirred for additional 1 hour. The reaction was quenched with an aqueous saturated ammonium chloride solution and extracted with hexane (30 ml*3). The organic layer was concentrated and the residue was purified by column chromatography (SiO2 60 g, elute: Hex/AcOEt=300/1) to give the titled compound as a colorless liquid (1.0g, 4.6mmol). Yield: 58% 1H NMR(CDCl3)delta 7.84-7.82(2H, m), 7.36-7.26(2H, m), 6.00-5.92(1H, m), 5.12-5.06(2H, m), 3.43(2H, d, J = 6.7 Hz), 1.60(9H, s).

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; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1728792; (2006); A1;,
Ester – Wikipedia,
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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. 69038-74-0, name is tert-Butyl 3-Bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H13BrO2

Example 36E tert-butyl 5′-amino-2′-methyl[1,1′-biphenyl]-3-carboxylate A mixture of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.00 g, 19.8 mmol) and tert-butyl 3-bromobenzoate (5.08 g, 19.8 mmol) in 1,4-dioxane (110 mL) and water (30 mL) was degassed under a N2 flow for 40 minutes. Potassium carbonate (13.7 g, 99 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (816 mg, 1.00 mmol) were added, and the mixture stirred at 80° C. for 7 hours. Water was then added to the reaction mixture, and it was extracted with ethyl acetate (2*). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography using a Biotage® SNAP 340 g silica column, eluted with 10-25percent ethyl acetate in iso-hexane, to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 7.97-7.93 (m, 2H), 7.49-7.41 (m, 2H), 7.06 (d, J=8.0 Hz, 1H), 6.64 (dd, J=2.4, 8.0 Hz, 1H), 6.60 (d, J=2.4 Hz, 1H), 3.60 (broad s, 2H), 2.14 (s, 3H), 1.60 (s, 9H).

According to the analysis of related databases, 69038-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
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. 69038-74-0, name is tert-Butyl 3-Bromobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 69038-74-0

General procedure: To a mixture of boronic acid ester 10 (2.5 mmol) and aryl bromide (1 mmol) in DME (20 mL) were added dichlorobis(triphenylphosphine)palladium (0.05 mmol) and 2 M aqueous Na2CO3 (5 mL), then the mixture was refluxed for 4 h. The mixture was cooled to ambient temperature and diluted with AcOEt, then washed with water, brine, dried over sodium sulfate, and filtered. After the filtrate was concentrated, the crude material was purified by silica gel column chromatography to give compounds 12a-12f.

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:
Article; Sakamaki, Shigeki; Kawanishi, Eiji; Nomura, Sumihiro; Ishikawa, Tsutomu; Tetrahedron; vol. 68; 29; (2012); p. 5744 – 5753;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 69038-74-0, These common heterocyclic compound, 69038-74-0, name is tert-Butyl 3-Bromobenzoate, 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.

(+)-Pinanediol 3-(teri-butoxycarbonyl)benzeneboronate (12b). A solution of tert- butyl 3-bromo-benzoate (1.70 g, 6.61 mmol), obtained from 3-bromobenzoic acid, (Wright, S. W. et al, Tetrahedron Lett. 1997, 38, 7345-7348) and freshly distilled triisopropyl borate (1.53 mL, 6.61 mmol) in THF (17 mL) was cooled to -100 °C under argon flow and w-butyllithium (2.5 M soln in hexane, 2.91 mL, 7.27 mmol) was added dropwise over 15 min, during which the solution turned cherry red. After 1 h at -100 °C, trimethylsilyl chloride (0.84 mL, 6.61 mmol) was dropped into the reactor and the resulting colorless solution was allowed to warm to room temperature and stirred overnight. Finally, (+)-pinanediol (1.12 g, 6.61 mmol) was added and the solution stirred 1 h at room temperature. The mixture was partitioned between ethyl acetate (100 mL) and water (40 mL) and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The combined organic phases were washed with brine, dried over MgS04, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (light petroleum/ethyl ether 95:5), affording 12b as a yellowish solid (2.10 g, 89percent yield). Mp 70-71 °C. [CC]D +7.3 (c 1.1, CHCI3). XH-NMR (400 MHz, CDC13): delta 0.94 (3H, s, pinanyl CH»), 1.24 (1H, d, J 10.9, pinanyl Hendo), 1.36 (3H, s, pinanyl G¾), 1.53 (3H, s, pinanyl CH3), 1.64 (9H, s, f-Bu), 1.98-2.30 (5H, m, pinanyl protons), 4.51 (1H, dd, J 8.5, 2.0, CHOB), 7.46 (1Eta, t, J7.6, ¾), 8.0 (1Eta, d, J 7.6, H4), 8.12 (1H, d, J7.6, H6), 8.45 (1H, s, H2). 13C-NMR (100 MHz, CDCI3): delta 24.0, 26.5, 27.1, 28.2, 28.7, 35.5, 38.2, 39.5, 51.4, 78.4, 80.9, 86.5, 127.6, 131.5, 132.1, 135.7, 138.7, 169.5, CB not seen. EI-MS: m/z 356 (M+, 10percent), 300 (36), 283 (41), 231 (50), 204 (38), 83 (65), 67 (59), 57 (100). Anal. Calcd. for C2iH29B04: C, 70.80; H, 8.20. Found: C, 70.55; H, 8.22.

The synthetic route of 69038-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI MODENA E REGGIO EMILIA; SHOICHET, Brian K.; PRATI, Fabio; CASELLI, Emilia; ROMAGNOLI, Chiara; EIDAM, Oliv; WO2013/56163; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics