Benzyl Bromide → 1-(Benzyloxy)-3-bromo-5-chlorobenzene

Participants

Reaction Steps

2.54 g 3-Bromo-5-chloro-phenol was dissolved in 50 mL acetone. Subsequently were added 8.04 g potassium carbonate, 1.52 mL benzyl bromide and 0.86 g tetrabutylammonium iodide. The mixture was refluxed for 2 h., cooled to room temperature and filtrated, and the filtrate was concentrated to dryness. The residue was chromatographed over a short column of silica, eluting with DCM/PA 1:4, and the pink color of the product fractions (at the front) was removed with active carbon. After filtration and evaporation, 3.11 g (90%) of a pale yellow oil was obtained. 1H NMR (400 MHz, CDCl3) δ 5.03 (s, 2H), 6.92 (t, J=2 Hz, 1H), 7.03 (t, J=2 Hz, 1H), 7.12 (t, J=1.5 Hz, 1H), 7.31-7.45 (m, 5H).

Provenance & Evidence