Hydrochloric Acid → HCID 86666500, compound

Participants

Reaction Steps

2.5M n-Butyllithium in hexanes (0.47 mL, 1.2 mmol) was added dropwise to a solution of 1-[3-bromo-5-(trifluoromethyl)phenyl]-N,N-dimethylmethanamine (0.30 g, 1.1 mmol, from Step A) in THF (6.0 mL) at −78° C. After stirring at this temperature for 20 minutes, N,N-dimethylformamide (160 μL, 2.1 mmol) was added dropwise. After a total reaction time of 50 minutes at −78° C., the reaction was quenched with 1.0M Hydrogen chloride in water (2.1 mL, 2.1 mmol). After warming to room temperature, the mixture was diluted with more water, treated with saturated sodium bicarbonate to achieve pH 7, then extracted with ethyl acetate (EtOAc). The combined extracts were washed with water (3×), brine, dried over sodium sulfate and concentrated to give a light yellow oil, a 4:1 mixture of the desired together with de-bromination byproduct, which was used without further purification (0.2 g, 60%).

Provenance & Evidence