Triethylamine → 4-Nitrophenylthiol acetate

Participants

Reaction Steps

To the solution of 5 ml (69.95 mmol) of thiolacetic acid and 12 ml of triethyl amine in 75 ml of toluene was added dropwise 7.5 g (34.71 mmol) of 4-nitrobenzyl bromide in 100 ml of 1:2 THF/Toluene for 4 hours. The mixture was continuously stirred overnight, evaporated and crystallized with EtAc/Toluene/Hexane to afford 7.1 g (96%) of the title compound. 1H NMR (CDCl3) 8.13 (ddd, 2H, J=2.5, 4.5, 9.3 Hz), 7.44 (ddd, 2H, J=2.5, 4.5, 9.3 Hz), 4.14 (s, 2H), 2.35 (S, 3H); 13C NMR 194.53, 145.73, 129.91, 124.07, 32.93, 30.50; MS M+234.34 (M+Na).

Provenance & Evidence