Sodium Hydroxide → Tert-butyl 3-(1-amino-2,2,2-trifluoroethyl)-5-bromobenzoate

Participants

Reaction Steps

To a solution of tert-butyl 3-bromo-5-(trifluoroacetyl)benzoate (3.0 g, 8.5 mmol) in toluene (mL) was slowly added lithium bis(trimethylsilyl)amide (1.0 M in toluene; 25.5 mL, 25.5 mmol). The reaction was stirred at ambient temperature. After 1 h, the reaction was checked by TLC for disappearance of tert-butyl 3-bromo-5-(trifluoroacetyl)benzoate. Borane dimethyl sulfide complex (2.0 M in toluene; 25.5 mL, 51.0 mmol) was added and the mixture was stirred at ambient temperature. After 1 h, aqueous NaOH (1.0 M) was added slowly to quench the reaction. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate) gave the title compound (1.48 g).

Provenance & Evidence