Phosphorus oxychloride → (6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Participants

Reaction Conditions

Reaction Steps

Phosphoryl chloride (50 mL, 0.547 mol) was cooled to 0° C. and (6-bromo-4-hydroxyquinolin-3-yl)(cyclopropyl)methanone (21 g, 67.7 mmol) was added. The reaction mixture was stirred at 0° C. for 2 h, at room temperature for 2 h and concentrated. The residue was dissolved in methylene chloride and poured into cold 30% aq. ammonium hydroxide. The aqueous layer was separated and extracted with methylene chloride. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by a silica plug to afford the desired product (5.8 g, 22%) as a brown solid: 1H NMR (300 MHz, CDCl3) δ 8.91 (s, J=6.4 Hz, 1H), 8.55-8.49 (m, 1H), 8.07-7.97 (m, 1H), 7.91 (dd, J=8.9, 2.1 Hz, 1H), 2.69-2.54 (m, 1H), 1.50-1.40 (m, 2H), 1.28-1.19 (m, 2H).

Provenance & Evidence