Ethyl Acetate → HCID 18979100, compound

Participants

Reaction Steps

The intermediate 8-methoxy-2-(trifluoromethyl)quinoline (2.21 g, 9.7 mmol) in MeOH (15 mL) was treated with a 1.5 N solution of bromine in MeOH (7.8 mL, 11.7 mmol) over a 15 min period. This mixture was stirred 2 h then treated with a 1 N aqueous solution of Na2S2O3 (30 mL) and EtOAc (300 mL). The phases where separated and the organic portion washed with brine, a saturated aqueous solution of NaHCO3, and again with brine. The organic phase was dried with Na2SO4, filtered, and evaporated to afford titled compound as a light brown solid. 1H NMR (CDCl3) 8.70 (dd, J=8.8, 0.6, 1H), 7.86 (d, J=8.8, 1H), 7.85 (d, J=8.4, 1H), 7.02 (d, J=8.4, 1H), 4.10 (s, 3H). LC/MS (Method B) 3.82 min, [M+1]+ 305/307.

Provenance & Evidence