反应详情

To a solution of 4-formylphenylboronic acid (100 g, 0.67 mol) and 2-chloro-5-(trifluoromethyl)pyridine 2 (121 g, 0.67 mol) in acetonitrile (900 mL) was added Pd(dppf)Cl2 (24 g, 33.5 mmol) and 2M aqueous Na2CO3 (837 mL). The resulting mixture was heated at reflux for 3 h under nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate (3*500 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give 4-(5-(trifluoromethyl)pyridin-2-yl)benzaldehyde (115 g) as a light yellow solid. 1H NMR (400 MHz CDCl3) δ10.04 (s, 1H), 8.92 (s, 1H), 8.15 (d, J=8.0 Hz, 2H), 7.98 (d, J=8.0 Hz, 1H), 7.96 (d, J=8.0 Hz, 2H), 7.86 (d, J=8.0 Hz, 1H). MS (M+1)=252.0.

1. temperatureThe resulting mixture was heated
2. temperatureat reflux for 3 h under nitrogen atmosphere
3. extractionThe reaction mixture was extracted with ethyl acetate (3*500 mL)
4. dry with materialThe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude material was purified by silica gel chromatography