反应详情

温度

90 °C

Alternative procedure: 2,3,5,6-Tetrafluoro-4-bromoaniline (12.0 g, 49.2 mmol) is dissolved in DME (250 mL) and treated with 3-methoxyphenylboronic acid (7.5 g, 49.2 mmol), a catalytic amount of palladium(II) acetate (0.23 g, 1.0 mmol) and tri-o-tolylphosphine (1.22 g, 4.0 mmol). Potassium carbonate (13.6 g in 50 mL water) is added and the reaction mixture stirred, purged with nitrogen, then heated to 90° C. for 24 hours. After cooling to room temperature most of the DME is removed by rotary evaporator under high vacuum. The resulting material is partitioned between EtOAc (200 mL) and water (250 mL). The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator. The crude reaction product is purified by flash chromatography (9:1 hexanes/EtOAc, then 6:4 hexanes/EtOAc) to give 2,3,5,6-tetrafluoro-4-(3′-methoxyphenyl)aniline (m.p. 94–96° C.).

1. custompurged with nitrogen
2. temperatureAfter cooling to room temperature most of the DME
3. customis removed by rotary evaporator under high vacuum
4. customThe resulting material is partitioned between EtOAc (200 mL) and water (250 mL)
5. washThe organic layer is washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated by rotary evaporator
8. customThe crude reaction product
9. customis purified by flash chromatography (9:1 hexanes/EtOAc