N-bromobutanimide → 5-bromo-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide

Participants

Reaction Steps

Following the procedure as described in Preparation 19, making variations only as required to use N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide) in place of N-benzyl-3-methylfuran-2-carboxamide to react with N-bromosuccinimide, 5-bromo-N-(3-fluorobenzyl)-3-methylthiophene-2-carboxamide was obtained as a colorless solid in 89% yield: 1H NMR (300 MHz, CD3CN) δ 7.39-7.31 (m, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.08 (d, J=10.2 Hz, 1H), 7.02 (dd, J=8.5, 2.5 Hz, 1H), 6.98 (s, 1H), 4.48 (d, J=6.1 Hz, 2H), 2.42 (s, 3H); MS (ES+) m/z 328.1 (M+1), 330.1 (M+1).

Provenance & Evidence