N-bromobutanimide → 1-(3-Bromoprop-1-en-2-yl)-4-chlorobenzene

Participants

Reaction Steps

A mixture of 31.0 g (0.20 mol) of 4-chloro-α-methylstyrene, 38.0 g (0.21 mol) of N-bromosuccinimide, 3.9 g (0.02 mol) of p-toluenesulfonic acid monohydrate and 610 mL of THF was heated at reflux for 3 h and then concentrated at room temperature. The residue was partitioned between 400 mL of hexanes and 200 mL of H2O, the organic phase was washed twice with 100 mL H2O and dried (MgSO4). Removal of solvent gave 47.8 g of a yellow oil that was used without further purification. 1H NMR (CDCl3, 200 MHz) δ4.33 (s, 2H), 5.50 (d, 2H), 7.2-7.5 (m, 5H).

Provenance & Evidence