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

Participants

Reaction Steps

To a solution of 128 g (470 mmol) of tert-butyl 3-bromophenylcarbamate in 800 mL of dimethylformamide, 19 g (475 mmol) of sodium hydride (60% in oil) are added portionwise and the reaction medium is stirred until the evolution of gas has ceased. 29.3 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 and evaporated. 152.5 g (92%) of tert-butyl 3-bromophenyl-N-methylcarbamate are obtained.

Provenance & Evidence