Triethylamine → 2-(Chloromethyl)-4-methoxy-1-nitrobenzene

Participants

Reaction Steps

MsCl (1.9 mL, 24 mmol) was added to Et3N (4.5 mL, 32 mmol) and 5-methoxy-2-nitrobenzyl alcohol (1.48 g, 8.1 mmol) in CH2 Cl2 (80 mL) and the mixture kept at reflux for 12 h. The solution was cooled, washed with dilute HCl (2N, 2×50 mL), dried (Na2 SO4), concentrated, and filtered through a short column of silica (eluting with 9:1 petroleum ether:EtOAc) to give 5-methoxy-2-nitrobenzyl chloride as a yellow liquid (1.55 g, 95%). 1H NMR (CDCl3) δ 8.17 (d, J=9.1 Hz, 1H, H-3), 7.20 (d, J=2.8 Hz, 1H, H-6), 6.93 (dd, J=9.1, 2.8 Hz, 1H, H-4), 5.03 (s, 2H, ArCH2Cl), 3.93 (s, 3H, ArOCH3); 13C NMR (CDCl3) δ 163.7 (C-2), 140.7, 135.5, 128.2, 116.5, 113.7 (C-1,3,4,5,6), 56.1 (OCH3), 43.7 (CH2Cl); MS (EI) m/z 201 [70%, M+ (35Cl)], 184 (100%), 166 (60%, M--Cl), 156 (50%), 106 (70%); HRMS (EI) Calcd. for C8H8 ClNO3 203.0163 (35Cl). Found 203.0165.

Provenance & Evidence