Chloroacetone → HCID 118006045, compound

Participants

Reaction Steps

A mixture of cloroacetone (17 mmol), LiBr (17 mmol) in acetonitrile (10 mL) was stirred at room temperature for 15 min. Then, a solution of 2-bromo-3-methylpyridine (19 mmol) in acetonitrile (10 mL) was added and the resulting mixture was heated at reflux for 24 h. The mixture was cooled to room temperature and the solvent was removed under reduce pressure. The residue was diluted with water extracted with diethylether. The aqueous was treated with K2CO3 (96 mmol) and heated at 80° C. for 2 h. The mixture was cooled to room temperature and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 35. (34%) 1H NMR (400 MHz, CDCl3) δ 7.76 (dt, J=6.9, 0.8 Hz, 1H), 7.20-7.07 (m, 1H), 6.83 (dd, J=7.1, 0.7 Hz, 1H), 6.40 (s, 1H), 6.25 (t, J=7.0 Hz, 1H), 2.39 (s, 3H). LC-MS (ES) for C9H8BrN [M+1]+ 209.11.

Provenance & Evidence