N-bromobutanimide → HCID 18456634, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-chloro-4-methoxy-phenyl)-N-methyl-acetamide (70a) (0.22 g, 1.03 mmol), NBS (183 mg, 1.03 mmol), and 70% benzyl peroxide (36 mg, 0.103 mmol) in 6 mL of CCl4 was refluxed at 80° C. for three hours, cooled to room temperature, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with 1:1 EtOAc and hexanes to provide 185 mg white solid as the intermediate 70b. 1H NMR (300 MHz, CDCl3) δ 7.42 (d, 1H, J=8.85 Hz), 6.90 (d, 1H, J=2.63 Hz), 6.83–6.76 (m, 1H), 5.83 (s, 1H), 3.78 (s, 3H), 2.90 (d, 3H, J=4.90 Hz). LCMS (ESI+) [M+H]/z Calc'd 294, found 294.

Provenance & Evidence