Benzoyl Peroxide → 6-Bromoquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of commercially available 6-bromo-1,2,3,4-tetrahydro-2-quinolinone (5.0 g, 22 mmol) and NBS (4.9 g, 27 mmol) in CHCl3 (80 mL) was added a catalytic portion of benzoyl peroxide at RT. The mixture was refluxed at 80° C. for 3 h, after which additional NBS (2.0 g) was added and the reaction refluxed overnight at 80° C. Additional NBS (0.9 g) was added into the reaction mixture which was refluxed at 80° C. for 5 h. The solid was filtered, washed with EtOH and dried to yield 6-bromoquinolin-2(1H)-one (4.35 g, 88% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 7.93 (d, J=2.8 Hz, 1H), 7.88 (d, J=9.6 Hz, 1H), 7.64 (dd, J=2.0, and 8.8 Hz, 1H), 7.25 (d, J=8.8 Hz, 1H), 6.55 (dd, J=2.0, and 9.6 Hz, 1H); LC-MS (EI) m/z: 224.0 (M+H+).

Provenance & Evidence