Allyl bromide → HCID 14838649, compound

Participants

Reaction Steps

A mixture of methyl 4-chloro-2-hydroxybenzoate (2f) (96.3 g, 0.52 mol), allyl bromide (134 ml, 1.55 mol) and ground potassium carbonate (107 g, 0.77 mol) in 1500 ml of dry acetone was heated under reflux for 20 hours. The inorganic salt was removed by filtration, and the solvent and excess allyl bromide evaporated to dryness to give 3f (117 g, 99.6% yield) as a yellow solid, mp 47°-55° C. NMR (CDCl3) δ 7.73 (d, 1H, J=8 Hz, aromatic proton meta to Cl), 6.97 (m, 2H, aromatic protons alpha to Cl), 6.40-5.17 (m, 3H, olefinic orotons), 4.57 (m, 2H, CH2) and 3.90 (s, 3H, CH3).

Provenance & Evidence