N-bromobutanimide → HCID 44549796, compound

Participants

Reaction Steps

A mixture of 161 (4.47 g, 13.91 mmol) and NBS (2.72 g, 1528 mmol) in MeCN (80 mL) was stirred at reflux for 3 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, to give tert-butyl 1-bromo-6-(methylsulfonyl)-2-naphthylcarbamate (162) (4.79 g, 86%) as a white solid: mp (MeOH) 190° C.; 1H NMR [(CD3)2SO] δ 8.95 (s, 1H), 8.61 (d, J=1.8 Hz, 1H), 8.36 (d, J=9.0 Hz, 1H), 8.22 (d, J=8.8 Hz, 1H), 8.08 (dd, J=9.0, 1.9 Hz, 1H), 7.96 (d, J=8.9 Hz, 1H), 3.25 (after D2O exchange, s, 3H), 1.50 (s, 9H). Anal. (C16H18BrNO4S) C, H, N.

Provenance & Evidence