Hydrochloric Acid → 1-(4-n-Propylphenyl)-1,2,2-trifluoroethylene
Reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C([Li])CCC.[F:16][C:17]([F:21])=[C:18](F)[F:19].Cl>CCCCCC.C(OCC)C>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:18]([F:19])=[C:17]([F:21])[F:16])=[CH:6][CH:5]=1)[CH2:2][CH3:3]Participants
Conditions
- Temperature
- -80 °C
Procedure
In 1 l four-necked flask having a gas supplying tube, 200 ml of n-hexane, 75 ml of dry diethyl ether and 24.6 g (0.1 mol) of 4-(n-propyl)iodobenzene were introduced under a nitrogen atmosphere, and then 86.2 ml of a hexane solution of n-butyl lithium (1.16 mol) was dropwise added thereto under stirring at -80° C. Then, while the reaction system was maintained at -80° C., 10 g (0.1 mol) of tetrafluoroethylene was introduced under vigorously stirring in 30 minutes. The reaction solution was stirred further for one hour and poured into ice water and neutralized with dilute hydrochloric acid, and then the organic layer was separated. The aqueous layer was extracted with methylene chloride, and the extract was combined to the organic layer, followed by drying. The solvent was distilled off to obtain 12 g (yield: 60%) of 1-(4-n-propylphenyl)-1,2,2-trifluoroethylene.
Workup
- customIn 1 l four-necked flask having
- temperatureThen, while the reaction system was maintained at -80° C.
- stirringunder vigorously stirring in 30 minutes
- stirringThe reaction solution was stirred further for one hour
- customthe organic layer was separated
- extractionThe aqueous layer was extracted with methylene chloride
- customby drying
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-8099d52e04994bb5b94ec3dd97063c50
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380461
Reaction notes
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