Triphenylphosphane dibromide → 4-Bromo-6-chloro-8-methylquinoline

Participants

Reaction Steps

A mixture of 6-chloro-4-hydroxy-8-methylquinoline (1.9 g, 9.8 mmol) and triphenylphosphine dibromide (6.2 g, 14.7 mmol) in acetonitrile (50 mL) was refluxed for 2 hours. The mixture was allowed to cool to room temperature then concentrated. The residue was purified by silica gel chromatography eluting with 0-10% EtOAc/hexanes to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.67 (d, J=4.7 Hz, 1H); 8.06 (d, J=2.2 Hz, 1H); 7.71 (d, J=4.6 Hz, 1H); 7.58 (s, 1H); 2.79 (s, 3H); LC1: 1.88 min. (M+H) 256.

Provenance & Evidence