HCID 59235385, compound → HCID 59235403, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-chloro-4-fluoro-N-methoxy-N-methylbenzamide (936 mg, 3.17 mmol) in tetrahydrofuran (15 mL) was added (4-ethylphenyl)magnesium bromide (9.5 mmol, 9.5 mL, 1 M in tetrahydrofuran) at 0° C. The mixture was stirred at 25° C. for 1 hour, then the reaction was quenched with saturated ammonium chloride, and most of the tetrahydrofuran was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water; the organic layer was separated, washed with water, then with brine, and dried over sodium sulfate. The sample was concentrated and then purified by preparative thin layer chromatography (petroleum ether:ethyl acetate, 4:1) to provide pure product 31a as a white solid (995 mg, 88% yield). 1H-NMR (CDCl3, 400 MHz): δ 7.71 (d, J=8.4 Hz, 2H), 7.58 (d, J=6.8 Hz, 1H), 7.31 (d, J=8.4 Hz, 2H), 7.26 (d, J=6.8 Hz, 1H), 2.73 (q, J=8 Hz, 2H), 1.27 (t, J=8 Hz, 2H).

Provenance & Evidence