Phosphorus tribromide → 4-[(1E)-3-bromo-1-propenyl]-4'-(trifluoromethoxy)-1,1'-biphenyl

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Reaction Steps

PBr3 (26 μL, 0.28 mmol) was added to a solution of alcohol 101 (0.159 g, 0.540 mmol) in Et2O (10 mL) at 0° C. The mixture was warmed to room temperature and stirred for 1 h, then quenched with ice and extracted with Et2O. The organic fraction was dried and evaporated, and then column chromatography of the residue on silica gel (eluting with CH2Cl2) gave 4-[(1E)-3-bromo-1-propenyl]-4′-(trifluoromethoxy)-1,1′-biphenyl (102) (0.123 g, 71%) as a white solid: mp 121-123° C.; 1H NMR (CDCl3) δ 7.60 (d, J=8.8 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.46 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.8 Hz, 2H), 6.69 (d, J=15.6 Hz, 1H), 6.45 (dt, J=15.6, 7.8 Hz, 1H), 4.18 (dd, J=7.8, 0.9 Hz, 2H). APCI MS m/z 277 [M+H−HBr]+.

Provenance & Evidence