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Hydrochloric Acid → 1-(4-n-Propylphenyl)-1,2,2-trifluoroethylene

HRID 1768878
Notes
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Reaction equation

HRID 1768878 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8301TetrafluoroethyleneHCID 6125411-Iodo-4-propylbenzeneHCID 178418339Butyllithium

Product 1

HCID 200979981-(4-n-Propylphenyl)-1,2,2-trifluoroethyleneYield 60%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8058HexaneSolvent2×

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

  1. customIn 1 l four-necked flask having
  2. temperatureThen, while the reaction system was maintained at -80° C.
  3. stirringunder vigorously stirring in 30 minutes
  4. stirringThe reaction solution was stirred further for one hour
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with methylene chloride
  7. customby drying
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-8099d52e04994bb5b94ec3dd97063c50
Source dataset
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05380461

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes