反应详情

A stirred solution of 2-iodoaniline (5.0 g, 22.8 mmol), and 4-methylphenylboronic acid (3.1 g, 22.8 mmol) in tetrahydrofuran was treated under argon with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.37 g, 0.46 mmol), and a 5.0 N sodium hydroxide solution (9.1 mL, 45.7 mmol). The reaction mixture was heated under reflux for 24 hours, cooled to room temperature, and washed with a saturated, aqueous, sodium chloride solution. The aqueous phase was further extracted with ethyl acetate (3×). The combined organic phase was dried over anhydrous magnesium sulfate, and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:12) to yield the title compound (3.26 g, 17.8 mmol, 78%) as an orange oil;

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 24 hours
3. washwashed with a saturated, aqueous, sodium chloride solution
4. extractionThe aqueous phase was further extracted with ethyl acetate (3×)
5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
6. customthe solvent evaporated in vacuo
7. customThe crude product was purified by flash column chromatography on silica gel
8. washeluting with a mixture of ethyl acetate-hexane (1:12)