Benzoyl Peroxide → HCID 57989228, compound

Participants

Reaction Conditions

Reaction Steps

Benzoyl peroxide (0.085 g) was added to a suspension of 2-(5-methyl-2-(trifluoromethyl)phenyl)acetic acid (1.12 g) and N-bromosuccinimide (1.101 g) in chlorobenzene (18 mL), and the resulting mixture was heated at 100° C. under nitrogen for 80 minutes, then allowed to cool. The resulting mixture was diluted with ethyl acetate, washed three times with water, once with brine, then dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. The oil was dissolved in tetrahydrofuran (11 mL) and treated with a 2 molar solution of borane-methyl sulfide complex in THF (5.1 mL), portionwise over 2 minutes. The resulting mixture was stirred at room temperature overnight, then cooled in ice-water and quenched by the addition of methanol. The effervescing mixture was removed from the cooling bath, stirred at room temperature for 70 minutes, then concentrated in vacuo. The residue was purified by flash chromatography on silica eluted with 15% ethyl acetate in isohexane to afford the crude product as a yellow oil. Yield 0.919 g.

Provenance & Evidence