Benzene → 3-Bromobenzophenone

Participants

Reaction Steps

1.65 ml (12.50 mmol) 3-Bromobenzoyl chloride was dissolved in 10 ml of dry benzene. This solution was then added cautiously under stirring to a suspension of 2.00 g (15.00 mmol, 1.20 eq.) aluminum chloride in 20 ml dry benzene at 10° C. After the complete addition the resulting mixture was refluxed for 5 h. After quenching the mixture by adding water and conc. hydrochloric acid the aq. layer was extracted with ethyl acetate. The comb. org. fractions were dried over Na2SO4 and evaporated. Column chromatography (hexanes/ether (9+1)) yielded 3.02 g (11.55 mmol, 92.40%) (3-Bromo-phenyl)-phenyl-methanone as a white solid. Rf.(hexanes/ether (9+1))=0.40. 1H-NMR (500 MHz, CDCl3): δ=7.37 (t, 1H, J=7.88 Hz), 7.51 (m, 2H), 7.62 (tt, 1H, J1=7.41 Hz, J2=1.42 Hz), 7.72 (m, 2H), 7.79 (m, 2H), 7.94 (t, 1H, J=1.80 Hz).

Provenance & Evidence