Thionyl Chloride → 6-Bromo-5,5,6,6-tetrafluorohexanoyl chloride

HRID 338822Notes

Reaction equation

HRID 338822 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]([F:17])([F:16])[C:7]([F:15])([F:14])[CH2:8][CH2:9][CH2:10][C:11](O)=[O:12]>>[Br:5][C:6]([F:17])([F:16])[C:7]([F:15])([F:14])[CH2:8][CH2:9][CH2:10][C:11]([Cl:3])=[O:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 582609356-Bromo-5,5,6,6-tetrafluorohexanoic acid

Product 1

HCID 582609286-Bromo-5,5,6,6-tetrafluorohexanoyl chlorideYield 88%

Conditions

Temperature
50 °C

Procedure

In nitrogen atmosphere, 780 g (6.33 mol) of thionyl chloride was added to 1300 g (4.87 mol) of the 6-bromo-5,5,6,6-tetrafluorohexanoic acid obtained as discussed above, followed by stirring at 50° C. for 4 hours. Then distillation was conducted under reduced pressure thereby obtaining 1223 g of the objective 6-bromo-5,5,6,6-tetrafluorohexanoyl chloride in the form of a light yellow liquid (88% yield, 91% GC purity).

Workup

  1. customobtained
  2. distillationThen distillation

Sources & evidence

ORD record
ord-4f793668bf1d4667bbef9aeb1dcde0dc
Source dataset
uspto-grants-2014_11
Patent number
US08889888B2

Reaction notes

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