Phosphorus oxychloride → HCID 86687536, compound

Participants

Reaction Conditions

Reaction Steps

To a vial charged with a mixture of 7-bromo-5-methylquinolin-4-ol and 5-bromo-7-methylquinolin-4-ol (0.09 g, 0.378 mmol) was added acetonitrile (1.890 ml) followed by the addition of POCl3 (0.035 ml, 0.378 mmol). The mixture was heated to 90° C. for 1.5 hr. The mixture was dried under reduced pressure and the crude residue purified with a 25 g Interchim HP spherical silica column (15 μm spherical) (0 to 50%, 10% DCM throughout) providing adequate separation of regioisomers. The major, first eluting isomer was isolated cleanly to yield 7-bromo-4-chloro-5-methylquinoline (48 mg, 0.187 mmol, 49.5% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.02 (s, 4H) 7.46 (d, J=4.69 Hz, 1H) 7.50 (dd, J=2.01, 0.93 Hz, 1H) 8.15-8.19 (m, 1H) 8.67 (d, J=4.70 Hz, 1H). m/z (ESI) 256.1 (M+H)+.

Provenance & Evidence