5-Bromo-2-bromomethylbenzoic acid ethyl ester synthesis

Yield:950741-84-1 76%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 70; for 18 h;

Steps:

11.B

Step B: Synthesis of ethyl 5-bromo-2-(bromomethyl)benzoate as an intermediate; [0134] A mixture of ethyl 5-bromo-2-methylbenzoate (7.52 g, 30.9 mmol), N- bromosuccinimide (6.05 g, 34.0 mmol) and benzoyl peroxide (0.75 g, 3.10 mmol) in carbon tetrachloride (150 ml) was heated to 70 ⁰C in an oil bath for 18 h. The mixture was cooled to room temperature, and the solids were removed by filtration. The filtrate was then concentrated under reduced pressure and purified by flash chromatography (silica, gradient 1- 10%, ethyl acetate/hexanes) to afford ethyl 5-bromo-2-(bromomethyl)benzoate (7.57 g, 76%) as a clear oil: ¹H NMR (300 MHz, CDCl₃) 8.09 (d, J= 2.2 Hz, IH), 7.61 (dd, J= 8.3, 2.2 Hz, IH), 7.33 (d, J= 8.2 Hz, IH), 4.90 (s, 2H), 4.42 (q, J= 7.2 Hz, 2H), 1.43 (t, J= 7.1 Hz, 3H).

References:

WO2009/42907,2009,A1 Location in patent:Page/Page column 51-52