Diisopropylcarbodiimide → 4-Bromo-2-fluoro-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

Into a 1000-mL round-bottom flask, was placed a solution of 4-bromo-2-fluorobenzoic acid (50 g, 229.36 mmol, 1.00 equiv) in dichloromethane (600 mL), N-methoxymethanamine hydrochloride (25 g, 257.73 mmol, 1.10 equiv). To the resulting mixture was added DIC (32 g, 253.97 mmol, 1.10 equiv) at 0° C. The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched by the addition of water (500 mL). The solids were filtered out. The resulting solution was extracted with DCM (2×300 mL) and the organic layers combined. The resulting mixture was washed with water (2×300 mL), and sodium carbonate (1×300 mL). The resulting mixture was washed with brine (1×300 mL), then dried over anhydrous sodium sulfate and concentrated under vacuum to yield 4-bromo-2-fluoro-N-methoxy-N-methylbenzamide as colorless oil.

Provenance & Evidence