Ethyl 2-hydroxyisobutyrate → Ethyl 2-fluoroisobutyrate
Reaction equation
C1C=CN=CC=1.[FH:7].S(F)(=O)(=O)O.O[C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[F:7][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Into a 50-ml autoclave having a teflon-made internal cylinder were placed 9 ml of a hydrogen fluoride/pyridine mixture [hydrogen fluoride/pyridne =70/30 (wt/wt), containing about 300 mM of hydrogen fluoride] and 9.15 g (91.5 mM) of fluorosulfuric acid. The autoclave contents were cooled to 0° C. Thereto was added 4.0 g (30.5 mM) of ethyl 2-hydroxyisobutyrate. The resulting mixture was subjected to a reaction at 40° C. for 4 hours. After the completion of the reaction, the reaction mixture was poured into ice water. The resulting mixture was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate and subjected to vacuum distillation to remove methylene chloride. The resulting residue was subjected to distillation to obtain 2.1 g (yield: 52%) of ethyl 2-fluoroisobutyrate having a boiling point of 124°-126° C.