反应详情

Triphenylphosphine (0.99 g, 3.8 mmol) was added to a solution of the azide (0.86 g, 3.4 mmol) in THF (25 mL) at 0° C. After 5 min, the mixture was warmed to room temperature. After 18 h, the reaction was diluted with ammonium hydroxide (10 mL). After 3 h, the reaction was diluted with 3 M NaOH and stirred for 1 h. The reaction was acidified to pH 2 with 4 N HCl. The solution was then diluted with Et2O and the layers were separated. The aqueous layer was extracted with Et2O and then basified with 2 N NaOH. The basic aqueous solution was extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to yield an oily solid. The crude solid was diluted with Et2O (50 mL) and filtered. The filtrate was concentrated in vacuo to yield a pale yellow oil. Silica gel column chromatography using 20:1 CH2Cl2:MeOH as an eluent yielded 0.64 g (83%) of 5-chloro-2-trifluoromethoxy-benzylamine as a colorless oil. The product was not stable at room temperature and was used for the next step immediately.

1. waitAfter 18 h
2. waitAfter 3 h
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with Et2O
5. extractionThe basic aqueous solution was extracted with CH2Cl2 (3×50 mL)
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield an oily solid
10. filtrationfiltered
11. concentrationThe filtrate was concentrated in vacuo
12. customto yield a pale yellow oil