Water → 5-Bromo-2-chloroquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-Chloroquinoline (8) (1.0 g, 6.11 mmol) in 1:1 H2SO4 : H2O (30 ml) was added N-Bromosuccinimide (1.7 g, 9.55 mmol). The mixture was stirred at 35° C. for 38 h and then cooled. The solution was diluted with enough 50% NaOH (aq) to maintain pH<1 and the mixture was extracted with CH2Cl2. The combined organic layers were washed with sat. NaHCO3 (aq) and dried (MgSO4). Concentration of the solvent afforded a dark brown oil (0.078 g, 79%) which was sequentially purified by flash chromatography (85:15 Hexane:CH2Cl2) and MPLC (85:15 Hexane:CH2Cl2) to afford 9 (0.22 g, 15%) as a white amorphous solid (m.p. 71° -72° C.). 1H NMR d (ppm): 7.39 d (CH arom), 7.51 dd (CH arom), 7.74 d (CH arom), 7.91 d (CH atom), 8.37 d (CH arom).

Provenance & Evidence