Thionyl Chloride → 4-(Chloromethyl)-2-methoxy-1-nitrobenzene

Participants

Reaction Steps

A mixture of (3-methoxy-4-nitrophenyl)methanol (0.5 g, 2.73 mmol) and thionyl chloride (0.3 mL, 4.09 mmol) was heated at reflux for 12 h. The reaction mixture was concentrated under reduced pressure to afford the title compound as a tan solid, 0.55 g (100% yield). This material was used in successive reactions without further purification. 1H NMR (CD3OD, 400 MHz): δ 4.00 (s, 3H), 4.60 (s, 2H), 7.05 (dd, J=8.3, 1.8 Hz, 1H), 7.14 (d, J=1.5 Hz, 1H), 7.86 (d, J=8.3 Hz, 1H). MS (ESI): m/z 202.03 [M+H]+ (UPLC-TOF: polar—3 min).

Provenance & Evidence