Phosphorus oxychloride → 6-Bromo-1-chloro-isoquinoline

Participants

Reaction Steps

Phosphorus oxychloride (0.60 mL, 6.44 mmol) was added in one portion to a stirred solution of 6-bromoisoquinoline N-oxide (409 mg, 1.83 mmol) in CH2Cl2 (10 mL) and the mixture was heated at reflux for 6 hours. Excess solvents were evaporated in vacuo, the residue suspended in water (10 mL) and basified with 0.880 ammonia. This mixture was extracted with CH2Cl2 (2×25 mL) and the combined organics were dried over MgSO4 and evaporated in vacuo to leave the crude product. Purification by column chromatography upon silica gel using hexanes-EtOAc (90:10) as eluant gave 6-bromo-1-chloroisoquinoline (215 mg, 0.86 mmol) as a cream-coloured solid.

Provenance & Evidence