Methanol → 4-Bromo-3-fluoro-N-methyl-2-nitroaniline

Participants

Reaction Steps

A solution of N-(4-bromo-3-fluoro-2-nitrophenyl)-2,2,2-trifluoroacetamide (3.42 g, 10.3 mmol) and triphenylphosphine (3.79 g, 14.4 mmol) in tetrahydrofuran (31.0 mL) at 0° C. was treated with methanol (1.67 mL, 41.3 mmol) followed by dropwise addition of diisopropyl azodicarboxylate (2.84 mL, 14.4 mmol), and the resultant reaction mixture was stirred at RT for 2 h. The reaction mixture was quenched with water (10 mL), concentrated in vacuo to remove most of the THF. Water (200 mL) was added and the resultant mixture was extracted with ethyl acetate (200 mL). Layers were separated and the organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography (100% hexanes to 80% dichloromethane/hexanes) gave the desired product (2.46 g, 96%) as an orange solid. LCMS calculated for C7H7BrFN2O2 (M+H)+: m/z=249.0, 251.0. found: 248.9, 250.9.

Provenance & Evidence