N-Methylacetamide → N-[(4-Fluorophenyl)methyl]-N-methylacetamide

Participants

Reaction Steps

To a solution of NaH (6.86 g, 0.172 mole, 60% in mineral oil, 1.3 equiv) in THF (250 mL), add dropwise a solution of N-methylacetamide (11.6 g, 0.159 mole, 1.2 equiv) in THF (90 mL). After about 20 min, add 4-fluorobenzylbromide (25 g, 0.132 mole). Stir for about 62 hours then pour over ice water (300 mL) and extract with ethyl acetate (400 mL and 200 mL). Combine the organic layers and wash with water (300 mL), dry over Na2SO4, filter and concentrate to an oil. Dissolve the oil in acetonitrile and extract with hexane to remove the mineral oil to give 22.79 g N-methyl-N-(4-fluorobenzyl)acetamide: mp=48-54° C.; Rf=0.45 (4% MeOH/methylene chloride); 1H NMR (CDCl3) 7.27-6.93 (m, 4), 4.5 (d, 2), 2.91 (s, 3), 2.14 (s, 3).

Provenance & Evidence