Azobisisobutyronitrile → 2-(3-(Bromomethyl)-5-methylphenyl)acetic acid

Participants

Reaction Steps

NBS (3.12 g) was added portionwise over 1 hour to a solution of 2-(3,5-dimethylphenyl)acetic acid (3.6 g) and AIBN (0.015 g) in ethyl acetate (100 mL) at 50° C. under nitrogen. More AIBN (0.015 g) was added and the mixture was heated to reflux for 3 hours. The reaction mixture was washed with 10% aqueous sodium chloride solution (2×200 mL), dried over magnesium sulphate, filtered and evaporated. The crude material was purified by flash silica chromatography using 20% ethyl acetate in isohexane containing 1% acetic acid as solvent. Fractions containing the product were evaporated to dryness to afford a solid which was triturated with cyclohexane (10 mL) to yield the subtitled compound as a white solid. Yield 2.10 g.

Provenance & Evidence