Thionyl Chloride → 5-Bromo-2-chloromethyl-4-methoxy-3-methyl-benzofuran

Participants

Reaction Steps

To a solution of (5-bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanol in 7 mL of dichloromethane was added 0.5 mL of thionyl chloride at room temperature. After 2 h the reaction was concentrated in vacuo, diluted with ethyl acetate and washed with water. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo to give 216 mg (92%) of 5-bromo-2-chloromethyl-4-methoxy-3-methyl-benzofuran. 1H NMR (400 MHz, CDC3) δ ppm 2.4 (s, 3 H) 3.9 (s, 3 H) 4.7 (s, 2 H) 7.1 (d, J=8.8 Hz, 1 H) 7.4 (d, J=8.6 Hz, 1 H).

Provenance & Evidence