Methyl 3-(Bromomethyl)-4-chlorobenzoate synthesis

Yield:220464-68-6 86.6%

Reaction Conditions:

with NBS;(E)-2,2'-(diazene-1,2-diyl)bis( 2-methylpropanenitrile);N-ethyl-N,N-diisopropylamine in Carbon tetrachloride at 80; for 16 h;

Steps:

15

To a solution of methyl 4-chloro-3-methylbenzoate (4.0 g, 21.67 mmol) in CCl4 (150 mL) was added NBS (4.6 g, 25.99 mmol) and the suspension was heated at 80 °C for 5 min and AIBN (1.78 g, 10.84 mmol) was added. The suspension was continued to stir at 80 °C for 16 h. The mixture was cooled to RT and filtered. The filtrate was concentrated to give the crude product, which was purified by silica gel chromatography eluting with EA/petroleum ether from 0% to 3% to give methyl 3-(bromomethyl)-4-chlorobenzoate (4.92 g, 86.6%) as a white oil.

References:

WO2018/169777,2018,A1 Location in patent:Paragraph 0235