Benzoic acid, 2-bromo-3-(dibromomethyl)-, methyl ester synthesis

Yield:1374020-60-6 98%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 75; for 3.5 h;Inert atmosphere;

Steps:

1.A Step A Methyl 2-bromo-3-(dibromomethyl)benzoate

To a solution of methyl 2-bromo-3-methylbenzoate (8.0 g, 34.2 mmol) in carbontetrachloride (100 mL) was added NBS (18.27 g, 103 mmol) followed by benzoyl peroxide (1.658 g, 6.85 mmol) and the mixture was stirred at 75°C under nitrogen atmosphere for 3.5 h. The mixture was concentrated, triturated with diethyl ether and filtered. The filtrate was dissolved in 1:1 diethylether/hexanes and washed with water. The organic phase was dried (Na2504), concentrated, driedvacuo to provide methyl 2-bromo-3-(dibromomethyl)benzoate (14.0 g, 34.8 mmol, 98 % yield) as a yellowish solid. 1H NMR (400 MHz, CHLOROFORM-d) 6 ppm 2.79 (s, 1 H) 3.97 (s, 3 H) 7.46 - 7.52 (m,H) 7.64 (dd, J=7.65, 1.63 Hz, 1 H) 8.20 (dd, J=8.03, 1.51 Hz, 1 H). LC/MS (m/z) ES: 386.9, 389.01).

References:

WO2017/2078,2017,A1 Location in patent:Page/Page column 30; 31