1,2-Dichlorobenzene → 3-fluoro-6-methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

To boron trifluoride etherate (1.29 g) at −12° C. under an atmosphere of nitrogen was added with stirring a solution of 3-amino-6-methoxyquinoline (1.05 g) in dry dichloromethane (15 ml). The yellow suspension was stirred for 15 minutes then a solution of t-butylnitrite (0.74 g) in dichloromethane (5 ml) was added dropwise. The mixture was stirred for 2 hours at 0° C. then 1,2-dichlorobenzene was added and the mixture gradually heated to 73° C., allowing the dichloromethane to distil out from the reaction vessel and then increased to 90° C. to complete the reaction. The mixture was allowed to cool to ambient temperature, diluted with dichloromethane, washed with water, dried over magnesium sulfate, filtered then evaporated under reduced pressure to give a black oil that was fractionated by chromatography (silica; hexane/ethyl acetate) to give an oil, 0.54 g, containing the required product. MH+178

Provenance & Evidence