Ethyl Acetate → 5-Bromo-2-chloro-8-methoxyquinoline

Participants

Reaction Steps

A solution of 8-methoxy-2-(chloro)quinoline CAS [74668-74-9] (1.0 g, 4.4 mmol) in MeOH (6.25 mL) was treated with a 1.5 N solution of bromine in MeOH (3.53 mL, 5.3 mmol) over 15 min period. The reaction mixture was stirred 2 h, treated with a 1 N aqueous Na2S2O3 solution (20 mL) followed by EtOAc (100 mL). The organic portion was washed with brine followed by a saturated aqueous solution of NaHCO3 followed by brine. The organic phase was dried over Na2SO4, filtered, evaporated, and purified by silica gel chromatography eluting with CH2Cl2 to afford titled compound as a colorless solid (49%). 1H NMR (CDCl3) 8.44 (dd, J=8.8, 1.2, 1H), 7.73 (dd, J=8.4, 1.2, 1H), 7.51 (dd, J=8.8, 1.2, 1 H), 6.97 (d, J=8.4, 1H), 4.06 (s, 3H). LC/MS 3.45 min, [M+1]+ 271/273.

Provenance & Evidence