m-Chloroperbenzoic acid → Isoquinoline, 5-bromo-, 2-oxide

Participants

Reaction Steps

To a solution of 5-bromoisoquinoline (10.65 g, 51.19 mmol) in CH2Cl2 (250 mL), m-CPBA (9.717 g, 56.31 mmol) was added and the mixture refluxed for 20 h and allowed to cool to rt. The mixture was washed with sat Na2SSO3 (75 mL), then 3×1N NaOH, then brine. The organic layer was dried w/Na2SO4, filtered and evaporated. The residue was crystallized from CH2Cl2: Et2O to yield the title compound as a white fluffy solid (4.58 g). MS (ESI pos. ion) m/z: 224 (MH+). Calc'd exact mass for C9H5BrNO: 224.

Provenance & Evidence