Methanol → HCID 22708819, compound

Participants

Reaction Steps

A mixture of intermediate (22) (0.23 mol), DCM (200 ml), methanol (70 ml) and CaCO3 (0.3 mol) was stirred at room temperature. N,N,N-trimethylbenzenemethanaminium dichlorideiodide (0.23 mol) was added portionwise. The reaction mixture was stirred and refluxed for 2 hours. The mixture was cooled, then taken up into water. This mixture was extracted with DCM. The combined organic layers were washed with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2). The desired fractions were collected and the solvent was evaporated, yielding 33.9 g 6-chloro-4-iodo-3-methoxy-2-methylbenzenamine (49.3%) (interm. 23).

Provenance & Evidence