N-bromobutanimide → HCID 44549921, compound

Participants

Reaction Steps

A mixture of 202 (2.05 g, 6.38 mmol) and NBS (1.31 g, 7.36 mmol) in MeCN (40 mL) was stirred at reflux for 2 h, then concentrated under reduced pressure. The residue was dissolved in CH2Cl2, and the solution was washed with 10% aqueous Na2SO3 and water, dried and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2Cl2/EtOAc (19:1), followed by recrystallization from MeOH to give tert-butyl 1-bromo-7-(methylsulfonyl)-2-naphthylcarbamate (203) (2.37 g, 93%) as a white solid: mp 166-167° C.; 1H NMR [(CD3)2SO] δ 8.99 (s, 1H), 8.70 (d, J=1.7 Hz, 1H), 8.25 (d, J=8.5 Hz, 1H), 8.10 (d, J=8.8 Hz, 1H), 8.00 (dd, J=8.5, 1.8 Hz, 1H), 7.97 (d, J=8.9 Hz, 1H), 3.32 (s, 3H), 1.50 (s, 9H). Anal. (C16H18BrNO4S) C, H, N.

Provenance & Evidence