Methyl iodide → Methyl 2-fluoro-4-formylbenzoate

Participants

Reaction Steps

Sodium hydride (69 mg, 1.7 mmol) was added portionwise to a solution of 2-fluoro-4-formylbenzoic acid (0.30 g, 1.4 mmol) in N,N-Dimethylformamide (5.0 mL) at 0° C. The mixture was allowed to warm to room temperature and was stirred for 30 minutes. Methyl iodide (0.18 mL, 2.9 mmol) was introduced dropwise. After 2 hours, the mixture was quenched with 1 N HCl, and extracted with EtOAc. The extracts were washed with water (twice), brine (once), dried over sodium sulfate and concentrated. Flash column chromatography, eluting with a gradient from 0-15% ethyl acetate in hexanes afforded product as a white solid (190 mg, 72%). 1H NMR (300 MHz, CDCl3): δ 10.05 (d, 1H), 8.11 (dd, 1H), 7.73 (dd, 1H), 7.65 (dd, 1H), 3.98 (s, 3H); LCMS (M+H)+: 183.0.

Provenance & Evidence