Nitrogen → 1-chloro-2,3,4-trimethoxy-benzene

Participants

Reaction Steps

To a stirred suspension of 3,4,5-trimethoxyaniline (6.27 g, 34.2 mmol) in 37% HCl:H2O (75:25) at 0° C. was added dropwise a solution of NaNO2 (2.51 g, 36.4 mmol) in H2O. The temperature was maintained below 5° C. during the addition. Upon complete addition of NaNO2, an ice cold solution of CuCl (4.41 g, 44.6 mmol) in 37% HCl was added and the solution allowed to warm to room temperature. The stirred suspension was warmed to 60° C. until evolution of N2 ceased. The product was filtered and washed with cold H2O. The crude product was purified by flash chromatography (silica gel, EtOAc/Petroleum Spirit 3:17) to give the title compound as a white solid (4.68 g, 67%). 1H NMR (300 MHz, CDCl3) δ 6.58 (s, 2H), 3.85 (s, 6H), 3.82 (s, 3H), ESIMS m/z [M+H]+ 203.2.

Provenance & Evidence