反应详情

温度

40 °C

2-(5-Chloro-2-methoxyphenyl)-1,1,1-trifluoropropan-2-ol (C45) (1.20 g, 4.71 mmol) was treated with thionyl chloride (4 mL, 50 mmol), followed by pyridine (19.1 μL, 0.236 mmol). The reaction mixture was heated at 40° C. for 16 hours, then poured into a mixture of ice and saturated aqueous sodium bicarbonate solution. The resulting mixture was extracted with dichloromethane (3×50 mL), and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was determined by 1H NMR to be a mixture of product and an alkene side-product derived from elimination, in a roughly 4:1 ratio; this was used in the following step without additional purification. GCMS m/z 272 (M+). 1H NMR (400 MHz, CDCl3), product peaks only: δ 2.27 (br s, 3H), 3.86 (s, 3H), 6.90 (d, J=8.8 Hz, 1H), 7.33 (dd, J=8.8, 2.5 Hz, 1H), 7.69-7.73 (m, 1H).

1. extractionThe resulting mixture was extracted with dichloromethane (3×50 mL)
2. dry with materialthe combined organic layers were dried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. additiona mixture of product
6. customthis was used in the following step without additional purification