Methyl chloroformate → Methyl benzyl[2-(2-bromophenyl)ethyl]carbamate

Participants

Reaction Conditions

Reaction Steps

2.48 g of N-benzyl-2-(2-bromophenyl)ethanamine in solution in 50 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at 0° C. 1.2 cm3 of triethylamine are added to the reaction mixture, then 0.67 cm3 of methyl chloroformate is introduced using a syringe. The reaction mixture is kept stirring for 1 h at 0° C., then 5 h at a temperature close to 20° C. The reaction mixture is poured into a mixture containing ice, ethyl acetate and water. Stirring is continued for 10 min. The aqueous phase is extracted with ethyl acetate. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, then concentrated using a rotary evaporator under reduced pressure (5 kPa). The brown oil obtained is purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 70% cyclohexane/30% ethyl acetate). After concentrating the fractions under reduced pressure, 2.51 g of methyl benzyl[2-(2-bromophenyl)ethyl]carbamate are obtained in the form of an oil.

Provenance & Evidence