Boron trifluoride → 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

Participants

Reaction Conditions

Reaction Steps

A dry 3 liter, 4-necked round bottom flask equipped with a mechanical stirrer, thermometer, addition funnel and refluxing condenser was charged with of 5-Acetyl-8-benzyloxycarbostyril (50 gms/0.17 moles) and dry dichloromethane (1 liter) under argon. To this solution was added boron trifluoride etharate (25.7 ml/0.204 moles). The reaction mass was heated to reflux. To this reaction mass was added slowly solution of bromine (8.4 ml/0.17 moles) in dichloromethane (100 ml) at reflux in 4 hours. The mixture was refluxed for additional 30 minutes. The mass was cooled to 30° C. and adjusted to pH 8-9 using 10% aqueous potassium carbonate solution (470 ml).

Provenance & Evidence