Trimethylsilyl cyanide → 3-Chloro-4-fluorobenzyl cyanide

Participants

Reaction Steps

To a solution of 4-bromomethyl-2-chloro-1-fluoro-benzene (3.7 g, 16.5 mmol) in CH3CN (30 mL) was added trimethylsilyl cyanide (2.1 mL) and TBAF (4.8 g, 18.4 mmol). The resulting mixture was heated at reflux for 30 min. After cooling of the mixture to room temperature, it was extracted with EtOAc. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by silica gel flash column chromatography to give the title compound (1.7 g, 60.7%) as an oil.

Provenance & Evidence