Lithium Bromide → 1-(2-Bromopropyl)-3-methoxybenzene

Participants

Reaction Steps

A round-bottomed flask was charged with 1-methyl-2-[3-(methyloxy)phenyl]ethyl methanesulfonate (2) (90 g, 0.368 mol), LiBr (80 g, 0.92 mol), and acetone (650 mL). The reaction mixture was refluxed for 24 h under N2 and then cooled to room temperature. The reaction mixture was filtered and concentrated under reduced pressure to afford the crude product. The product was passed through a pad of silica gel to remove inorganic impurities. The product was distilled under reduced pressure (2-3 mm Hg) at 130-135° C. to afford ˜85 g (100%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 7.25 (dd, J1=8.00 Hz, J2=8.00 Hz, 1H), 6.84-6.78 (m, 3H), 4.32 (sextet, J=4.00 Hz, 1H), 3.82 (s, 3H), 3.25 and 3.21 (dd, J1=16.00 Hz, J2=8.00 Hz, 1H), 3.07 and 3.04 (dd, J1=16.00 Hz, J2=8.00 Hz, 1H), 1.71 (d, J=8.00 Hz, 1H).

Provenance & Evidence