methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate synthesis

Yield:955929-54-1 82%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;potassium acetate in 1,4-dioxane at 85; for 3 h;Inert atmosphere;Sealed tube;

Steps:

Methyl 2-methyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl) benzoate
To methyl 3-bromo-2-methylbenzoate (10.0 g, 43.7 mmol), bis(pinacolato)diboron (33.3 g, 131 mmol), potassium acetate (9.0 g, 91.7 mmol) in dioxane (100 mL), 1,4-[1,1-bis (diphenylphosphine) ferrocene] palladium dichloride-dichloromethane complex (3.2 g, 4.37 mmol) was added, and the mixture was reacted under argon atomsphere in sealed vessel at 85 °C for 3 hours. The cooled reaction mixture was diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, then filtered and concentrated. The crude product was purified with a silica gel column (eluted with ethyl acetate) to obtain the target compound A1 (10.0 g, 82%) as a yellow oil. ¹H NMR (400 MHz, DMSO-d₆) δ 7.87-7.82 (m, 2H), 7.26-7.19 (m, 1H), 3.88 (s, 3H), 2.74 (s, 3H), 1.35 (s, 12H).

References:

Shanghai Ennovabio Pharmaceuticals Co., Ltd.;JIANG, Lei;DENG, Jianwen;LU, Xiaoli;SHANG, Ke;SHOU, Jianyong;WANG, Bing;WU, Danyi;XU, Xueli;XU, Yuan;ZHANG, Yi;ZHENG, Mingwei EP3669872, 2020, A1 Location in patent:Paragraph 0089-0091

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