Allyl bromide → Allyl 1H,1H-perfluorooctyl ether

HRID 1760494Notes

Reaction equation

HRID 1760494 reaction equation
[C:1]([CH2:23][OH:24])([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([F:22])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[CH2:25](Br)[CH:26]=[CH2:27].[OH-].[K+]>CS(C)=O.O>[C:1]([CH2:23][O:24][CH2:27][CH:26]=[CH2:25])([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([F:20])([F:21])[F:22])([F:17])[F:18])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 67543(Perfluoroheptyl)methanol

Product 1

HCID 2735872Allyl 1H,1H-perfluorooctyl etherYield 75.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 124 g of C7F15CH2OH and 62 g of allyl bromide in 1240 g of dimethyl sulfoxide was dropwise added a solution of 28.1 g of potassium hydroxide in 35 g of water. The mixture was allowed to stir for 4 hr, during which time it separated into two immiscible liquid phases. The reaction mixture was poured into a separatory funnel, and the lower layer was isolated and washed 3 times with water to remove any remaining solvent. The crude product was dried over anhydrous magnesium sulfate, filtered, and vacuum distilled to yield 103 g of C7F15CH2OCH2CH═CH2 (E1), b.p. 88-89° C. at 30 torr (4 kilopascals (kPa)).

Workup

  1. customseparated into two immiscible liquid phases
  2. additionThe reaction mixture was poured into a separatory funnel
  3. customthe lower layer was isolated
  4. washwashed 3 times with water
  5. customto remove any remaining solvent
  6. dry with materialThe crude product was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationvacuum distilled

Sources & evidence

ORD record
ord-1e9f22b4f72845b1a81f227d4d960ed2
Source dataset
uspto-grants-2005_01
Patent number
US06841079B2

Reaction notes

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