Reacción #1362163

Ecuación de reacción

tert-butyl 3-bromomethyl-4-fluorobenzoate

2,2,2-trifluoroethylamine

→

title compound

Rendimiento 72.0%

tert-Butyl 4-fluoro-3-[(2,2,2-trifluoroethyl)aminomethyl]benzoate

Rendimiento 72.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated
2. 2
   Otrothe residue partitioned between Et2O and 10% K2CO3
3. 3
   LavadoThe organic phase was washed with 10% K2CO3 and brine
4. 4
   Otrodried
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by chromatography (silica gel, step gradient, 0-8% ethyl acetate/hexane)

Procedimiento

A mixture of tert-butyl 3-bromomethyl-4-fluorobenzoate (14 g, 48 mmol) and 2,2,2-trifluoroethylamine (25 g, 250 mmol) in THF (300 mL) was stirred under argon at RT for 4 d, concentrated, and the residue partitioned between Et2O and 10% K2CO3. The organic phase was washed with 10% K2CO3 and brine, dried, and concentrated. The residue was purified by chromatography (silica gel, step gradient, 0-8% ethyl acetate/hexane) to give the title compound as a pale yellow oil (10.7, 72%): MS (ES) m/e 308.3[M+H]+.

Fuente