tert-butyl 3-(bromomethyl)-4-fluorobenzoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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]+. concentrated the residue partitioned between Et2O and 10% K2CO3 The organic phase was washed with 10% K2CO3 and brine dried concentrated The residue was purified by chromatography (silica gel, step gradient, 0-8% ethyl acetate/hexane)