3-Methyl-2-nitrobenzoic acid → 3-Methyl-2-nitrobenzoyl chloride

Participants

Reaction Conditions

Reaction Steps

3-Methyl-2-nitrobenzoic acid 67 (30.0 g, 166 mmol, 1.0 equiv.) was suspended in CH2Cl2 (150 ml) and the suspension was cooled to 0° C. using an ice bath. Oxalyl chloride (2.0 M in CH2Cl2, 166 ml, 332 mmol, 2.0 equiv.) was added to the stirred reaction mixture through a pressure equalizing dropping funnel over 30 min. DMF (10 drops) was added dropwise. The reaction mixture was allowed to warm up to room temperature. After 30 min., the reaction was concentrated to dryness on a rotary evaporator. The solid material was re-dissolved in CH2Cl2 (200 ml) and was concentrated to dryness on a rotary evaporator to give 3-methyl-2-nitro-benzoylchloride 68 (32.9 g, 99%) as an off white solid.

Provenance & Evidence