反应详情

温度

100 °C

To a mixture of 2-bromo-1,4-naphthoquinone (1.0 g, 4.22 mmol), 4-hydroxyphenylboronic acid (640 mg, 4.64 mmol), potassium phosphate (3.135 g, 14.76 mmol), tricyclohexylphosphine (118 mg, 0.422 mmol), toluene (20 mL) and water (1 mL) was added palladium acetate (47 mg, 0.21 mmol) under N2. The reaction mixture was heated to 100° C. for 3 h. The reaction was cooled to rt and water was added. The mixture was extracted with EtOAc, and the combined organic extracts were washed with water and brine. The organic phase was separated, dried and concentrated to give crude product. Purification by column chromatography, using 10% EtOAc in hexane, gave 480 mg of 2-(4-hydroxy-phenyl)-[1,4]naphthoquinone (45%). MS (ES) m/z: 251.03 (M+1).

1. temperatureThe reaction was cooled to rt
2. extractionThe mixture was extracted with EtOAc
3. washthe combined organic extracts were washed with water and brine
4. customThe organic phase was separated
5. customdried
6. concentrationconcentrated
7. customto give crude product
8. customPurification by column chromatography