Trifluoroacetic acid → 1-Benzyl-3-bromobenzene

Participants

Reaction Steps

Under a nitrogen atmosphere, into a cold (10° C.) solution of trifluoroacetic acid (240 mL) was added a solution of 3-bromobenzophenone (11 g, 42.1 mmol) in CH2Cl2 (120 mL) over 10 minutes, followed by slow addition of NaBH4-pellets (19 g) over 1 hour. The reaction mixture was stirred at room temperature for 18 h, poured into ice, basified with NaOH (50%) to pH 8 and extracted with ether. The organic extracts were combined, dried over MgSO4, treated with charcoal and filtered. The filtrate was concentrated in vacuo to give 1-benzyl-3-bromobenzene as an oil (9.65 g, 92% yield) MS m/e (M+H)+ 248; 1H NMR (400 MHZ, DMSOd6) δ 3.89 (s, 2H,), 7.19-7.39 (m, 9H).

Provenance & Evidence