Ammonium Chloride → 3-AZIDO-1,1,1-TRIFLUOROPROPAN-2-OL

To a stirred solution of 1,1,1-trifluoro-2,3-epoxypropane (2.0 g, 18 mmol) in 70% ethanol (20 mL) was added ammonium chloride (1.9 g, 36 mmol) followed by sodium azide (2.3 g, 36 mmol). The reaction mixture was stirred at room temperature. After 6 h, the reaction mixture was partitioned between water (100 mL) and diethyl ether (100 mL). The organic layer was washed with additional water (100 mL). The first aqueous layer was back-extracted with diethyl ether (100 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give 3-azido-1,1,1-trifluoropropan-2-ol as a crude oil. 1H NMR (600 MHz, DMSO-D6) 4.14 (m, 1H); 3.58-3.49 (m, 2H); 2.58 (d, 1H).

1. customthe reaction mixture was partitioned between water (100 mL) and diethyl ether (100 mL)
2. washThe organic layer was washed with additional water (100 mL)
3. extractionThe first aqueous layer was back-extracted with diethyl ether (100 mL)
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-672260838ec04f779ef82eed9edd236c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183245B2