Ethyl Acetate → 1-(Bromomethyl)-4-(4-(trifluoromethoxy)benzyl)benzene

Participants

Reaction Steps

A solution of alcohol 95 (0.18 g, 0.64 mmol) in CH2Cl2 (4 mL) was treated with PBr3 (115 μL 1.2 mmol). The reaction mixture was stirred at room temperature for 2 h, then EtOAc (150 mL) was added. The organic layer was washed with water (100 mL), the aqueous layer was re-extracted with EtOAc (100 mL), and the combined organic layers were washed with brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with petroleum ether/EtOAc (9:1), to give 1-(bromomethyl)-4-[4-(trifluoromethoxy)benzyl]benzene (96) (0.14 g, 64%) as a white solid: mp (EtOAc/hexane) 33-35° C.; 1H NMR (CDCl3) δ 7.34-7.30 (m, 2H), 7.20-7.10 (m, 6H), 4.48 (s, 2H), 3.97 (s, 2H); HREIMS calcd for C15H1279BrF3O m/z (M+) 344.0024, found 344.0033; calcd for C15H1281BrF3O m/z (M+) 346.0003, found 346.0011.

Provenance & Evidence