[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].I[CH3:17].[H-].[Na+].OS([O-])(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6](=[O:15])[N:7]([C:8]1[CH:9]=[CH:10][C:11]([I:14])=[CH:12][CH:13]=1)[CH3:17])([CH3:4])([CH3:2])[CH3:3]
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).
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