Methyl iodide → N-Boc 4-Iodo-N-methylaniline

Participants

Reaction Steps

A solution of 15.96 g (50 mmol) (4-Iodo-phenyl)-carbamic acid tert-butyl ester and 24.96 ml (400 mmol) iodomethane in 250 ml THF was treated at −18° C. with 4.36 (100 mmol) 55% NaH during 1 h. The reaction was warmed up over night to room temperature, neutralized at 0° C. with aqueous 10% KHSO4, evaporated and extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to yield 17.8 g (quantitative) of (4-Iodo-phenyl)-methyl-carbamic acid tert-butyl ester, MS: 333 (M).

Provenance & Evidence