Thionyl Chloride → 4,6-Dichloro-2-(chloromethyl)benzofuran

Participants

Reaction Steps

To a solution of the product of Step E (0.24 g; 1.1 mmol) and DIPEA (0.2 ml; 1.11 mmol) in anhydrous THF (1 ml), SOCl2 (0.1 ml; 1.13 mmol) was added drop wise at 0° C. under N2 with stirring. The mixture was allowed to warm up to room temperature and stirred overnight, then diluted to 15 ml with Et2O and washed with 0.1N HCl, 5% NaHCO3, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure to give the title compound (0.25 g; 96%), as a creamy syrup, which was used in the next step without further purification. 1H-NMR (CDCl3) 4.68 (s, 2H); 6.8 (s, 1H), 7.2 (s, 1H); 7.39 (s, 1H).

Provenance & Evidence