Phosphorus oxychloride → 2-Chloro-5-(chloromethyl)-3-(trifluoromethyl)pyridine
反応式
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[C:6](OC)=[N:7][CH:8]=1.O=P(Cl)(Cl)[Cl:17]>CN(C=O)C>[Cl:17][C:6]1[C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][N:7]=1参加物
4
反応条件
- 温度
- 100 °C
実験手順
To a cold solution of 5-(chloromethyl)-2-methoxy-3-(trifluoromethyl)pyridine (0.3 g, 1.33 mmol) in DMF (0.6 mL) was added dropwise POCl3 (1.02 g, 6.65 mmol). The reaction was stirred for 1 h at 100° C. in a sealed tube. The reaction was cooled to room temperature, and poured onto ice water (10 mL). The reaction was extracted with DCM (thrice) and the combined organic layer was washed with water and brine, dried with MgSO4 and concentrated. The residue was purified by silica gel column chromatography to provide the title compound (0.20 g). LCMS m/z=230.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 4.62 (s, 2H), 8.06 (d, J=2.3 Hz, 1H), 8.57 (d, J=2.3 Hz, 1H).