Triphenylphosphane dibromide → 4-Bromo-7-chloroquinoline

Participants

Reaction Steps

A suspension of 7-chloroquinolin-4-ol (10.0 g, 55.7 mmol) and triphenylphosphine dibromide (35.3 g, 83.6 mmol) in CH3CN (370 mL) was refluxed for 16 hours then cooled to room temperature. The resulting precipitate was collected by vacuum filtration and washed with CH3CN (2×70 mL). The precipitate was then partitioned between CH2Cl2 (300 mL) and 1 M NaOH (aq) (300 mL). The aqueous phase was extracted with CH2Cl2 (100 mL). The combined organics were dried over Na2SO4, filtered, and concentrated to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.67 (d, J=4.7 Hz, 1H); 8.14 (d, J=9.0 Hz, 1H); 8.11 (d, J=2.1 Hz, 1H); 7.70 (d, J=4.7 Hz, 1H); 7.60 (dd, J=9.0, 2.1 Hz, 1H); LC4 1.86 min. (M+H)=244.

Provenance & Evidence