2,3,3,3-Tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoyl fluoride → 2,3,3,3-Tetrafluoro-2-(heptafluoropropoxy)propanoyl chloride

HRID 864612

Reaction equation

HRID 864612 reaction equation
[Al+3].[Cl-:2].[Cl-].[Cl-].[C:5]([C:9]([C:12]([O:15][C:16]([C:22](F)=[O:23])([C:18]([F:21])([F:20])[F:19])[F:17])([F:14])[F:13])([F:11])[F:10])([F:8])([F:7])[F:6]>ClC1C=CC=CC=1Cl>[C:5]([C:9]([C:12]([O:15][C:16]([C:22]([Cl:2])=[O:23])([C:18]([F:21])([F:20])[F:19])[F:17])([F:14])[F:13])([F:11])[F:10])([F:8])([F:7])[F:6]

Participants

4

Reactant 2

HCID 1027402,3,3,3-Tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoyl fluorideHCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
6 °C

Procedure

A mixture of AlCl3 and o-dichlorobenzene (4 mL) was treated with CF3CF2CF2OCF(CF3)COF (13.2 g, 40 mmol) and heated at 6 ° C. for 0.5 hr. Volatiles were removed by vacuum transfer (27 Pa) to give a mixture of two liquids. The lower layer was separated and distilled to provide 8.0 g of colorless liquid, bp ca. 65° C. GC analysis showed 99% purity. 19F NMR (F11): -81.32 (s, CF3), -81.94 (t, J=7.3 Hz, CF3), -79.05 and -84.98 (AB pattern, J=146 Hz, OCF2), -126.1 (d of m's, J=23, CF), -130.1 (s, CF2).

Workup

  1. customVolatiles were removed by vacuum transfer (27 Pa)
  2. customto give
  3. additiona mixture of two liquids
  4. customThe lower layer was separated
  5. distillationdistilled

Sources & evidence

ORD record
ord-980e72b584de4f12bf3dd64be91fee89
Source dataset
uspto-grants-1996_10
Patent number
US05563235

Linked notes

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