2,3,3,3-Tetrafluoro-2-(heptafluoropropoxy)propanoyl chloride → CF3CF2CF2Ocf(CF3)cho

HRID 864615Notes

Reaction equation

HRID 864615 reaction equation
[C:1]([C:5]([C:8]([O:11][C:12]([C:18](Cl)=[O:19])([C:14]([F:17])([F:16])[F:15])[F:13])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2]>[Pd]>[C:1]([C:5]([C:8]([O:11][C:12]([CH:18]=[O:19])([C:14]([F:16])([F:17])[F:15])[F:13])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2]

Participants

3

Reactant 1

HCID 27825972,3,3,3-Tetrafluoro-2-(heptafluoropropoxy)propanoyl chloride

Product 1

HCID 15717421CF3CF2CF2Ocf(CF3)choYield 53.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
0 °C

Procedure

A 3-necked round bottom flask equipped with a dropping funnel and reflux condenser was charged with 10% Pd/C (0.35 g) and cooled to 0° C. Triisoprolpylsilane (6.0 g) was added. CF3CF2CF2OCF(CF3)COCl (10.9 g) was added, and the mixture was stirred at 25° C. for 75 hr. During this period, a total of 0.5 g of additional catalyst was added in ca. 0.1 g increments. Vacuum transfer and separation of the lower layer after chilling at -25° C. provided 5.26 g of liquid. 1H NMR (THF-d8 /F11): 9.9 (m). 19F NMR: -79.4 (m), -81.1 (s), -81.4 (t, J=7.2), -129.5 (s), -138.8 (m). 1H-decoupling experiment showed JHCCF ca. 2.5 Hz.

Workup

  1. customA 3-necked round bottom flask equipped with a dropping funnel
  2. temperaturereflux condenser
  3. additionTriisoprolpylsilane (6.0 g) was added
  4. waitDuring this period
  5. customVacuum transfer and separation of the lower layer
  6. temperatureafter chilling at -25° C.

Sources & evidence

ORD record
ord-47f2cc846eb6461db44a6111f78a93c8
Source dataset
uspto-grants-1996_10
Patent number
US05563235

Reaction notes

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