Allyl bromide → 4,4,5,5,6,6,7,7,7-Nonafluorohept-1-ene

HRID 963587Notes

Reaction equation

HRID 963587 reaction equation
[F:1][C:2](I)([F:13])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[CH2:15](Br)[CH:16]=[CH2:17]>[Cu].CS(C)=O>[F:1][C:2]([F:13])([C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6])[CH2:17][CH:16]=[CH2:15]

Participants

5

Procedure

A mixture of perfluorobutyl iodide (103.8 g, 0.3 mol), copper powder (50 g, 0.79 mol) and dimethyl sulfoxide (150 mL) was stirred at 110°-120° C. for 2 hr, then cooled to room temperature. Allyl bromide (36.3 g, 0.3 mol) was added dropwise and then the mixture was stirred at room temperature for 2 hr and at 50° C. for 1 hr. The reaction mixture was distilled in vacuo and the crude product was collected in a cold trap (-78° C.). Redistillation produced 55.2 g (70% yield) of the desired 4,4,5,5,6,6,7,7,7-nonafluoro-1-heptene, formula above, having a boiling point of 79°-80° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr and at 50° C. for 1 hr
  2. distillationThe reaction mixture was distilled in vacuo
  3. customthe crude product was collected in a cold trap (-78° C.)
  4. distillationRedistillation

Sources & evidence

ORD record
ord-1d1b9226f3454e558aa674478fc26520
Source dataset
uspto-grants-1998_06
Patent number
US05763552

Reaction notes

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