Methyl iodide → N-BOC-N-Methyl-3-bromoaniline

Participants

Reaction Steps

To a solution of 129 g (475 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 mL of dimethylformamide are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29 mL (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate, filtered and evaporated. 115 g (95%) of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained.

Provenance & Evidence