N-[3-(bromomethyl)phenyl]acetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(3-(bromomethyl)phenyl)acetamide (6.6 g, 29 mmol) in CH3CN (50 mL) and water (10 mL) was added K2CO3 (6 g, 43 mmol) and EtSH (1.79 g, 29 mmol). The mixture was stirred at r.t. overnight. After removal of the solvent, the residue was extracted with EtOAc, dried and concentrated to give the crude product. The crude was purified by silica gel chromatography (petroleum ether:EtOAc=1:0 to 10:1) to give N-(3-(ethylthiomethyl)phenyl)acetamide (3.4 g, 56% yield) as a light yellow solid. 1H NMR: (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.41 (s, 1H), 7.34 (d, 1H), 7.22-7.17 (m, 1H), 7.01 (d, 1H), 3.61 (s, 2H), 2.41-2.34 (m, 2H), 2.11 (s, 3H), 1.24 (t, 3H). After removal of the solvent the residue was extracted with EtOAc dried concentrated to give the crude product The crude was purified by silica gel chromatography (petroleum ether:EtOAc=1:0 to 10:1)