Hydrochloric Acid → 3-Chloro-4-(cyanomethyl)benzoyl chloride

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-(bromomethyl)-3-chlorobenzoic acid (4.0 g, 16 mmol) in DMF (120 mL) and H2O (40 mL) was treated with NaCN (2.4 g, 49 mmol) and heated to 80° C. for 2 h. The mixture was cooled to rt and acidified with 1N HCl. The aqueous mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were concentrated under reduced pressure and dissolved in MTBE. The organic mixture was washed with H2O and brine (3×25 mL), dried over MgSO4, filtered and concentrated to afford 3-chloro-4-(cyanomethyl)benzoyl chloride.

Provenance & Evidence