Pyridine → HCID 59398571, compound

Participants

Reaction Conditions

Reaction Steps

4-Methyl-3-(trifluoromethyl)aniline (1.75 g, 10.0 mmol) was dissolved in DCM (10 mL), and pyridine (970 μL, 12.0 mmol) and then benzyl chloroformate (2 mL, 14.0 mmol) were dropwise added thereto. The resulting mixture was stirred at 0° C. for 0.5 hours. The organic layer was washed with a saturated sodium bicarbonate solution and saturated brine, sequentially, and then concentrated under reduced pressure. The residue was dissolved in 15 mL of carbon tetrachloride, and N-bromosuccinimide (2.67 g, 15.0 mmol) and 2,2-azobisisobutyronitrile (250 mg, 1.52 mmol) were added thereto. The resulting mixture was refluxed under heating for 1 hour. Insoluble substance was removed by filtration, and the filtrate was concentrated. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate 20:1) to give [4-bromomethyl-3-(trifluoromethyl)phenyl]carbamic acid benzyl ester (1.04 g, 27%) as a light-yellow oil.

Provenance & Evidence