Water → HCID 86707275, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium (289 mg, 0.250 mmol), potassium carbonate (829 mg, 6.00 mmol), water (4 mL) and 2,4,6-trivinylcyclotriboroxane-pyridine complex (722 mg, 3.00 mmol) were successively added to a solution of 2-bromo-4-fluoroaniline (950 mg, 5.00 mmol) in 1,2-dimethoxyethane (10 mL) under an argon atmosphere. The mixture was heated to an external temperature of 105° C. and stirred for 7 hr. The mixture was diluted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. Thereafter, the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→2:1) to afford 2-ethenyl-4-fluoroaniline as a reddish brown oil (458 mg).

Provenance & Evidence