Quinoline → 5-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

Participants

Reaction Steps

A mixture of 4-bromo-2-(2-chloro-1,1-dimethyl-ethyl)-1-methoxy-benzene (65 g, 0.234 mol), pyridine hydrochloride (121.8 g, 1.054 mol) and quinoline (110.67 mL, 0.936 mol) was refluxed at 164° C.–167° C. under argon for 5 hrs. After cooling to room temperature the reaction mixture was treated with ice-cold 6N HCl and extracted twice with ether. The organic layers were combined, dried (MgSO4), filtered and evaporated. The residue was purified on silica gel (10% ethyl acetate in hexane) to give 52 g of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (98%). 1H NMR (300 MHz; CDCl3): δ 1.32 (s, 6H), 4.23 (s, 2H), 6.67 (d, J=8.1 Hz, 1H), 7.19 (m, 2H).

Provenance & Evidence