Triethylamine → 2H-Perfluoroisopropyl 2-fluoroacrylate

HRID 968981Notes

Reaction equation

HRID 968981 reaction equation
[F:1][C:2](=[CH2:6])[C:3](Cl)=[O:4].[F:7][C:8]([F:16])([F:15])[CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11].C(N(CC)CC)C>O>[F:1][C:2](=[CH2:6])[C:3]([O:14][CH:9]([C:10]([F:13])([F:12])[F:11])[C:8]([F:16])([F:15])[F:7])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 27833352-Fluoroacryloyl chloride

Product 1

HCID 27783592H-Perfluoroisopropyl 2-fluoroacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12 g of 2-fluoroacryloyl chloride and 27 g of 1,1,1,3,3,3-hexafluoro-2-propanol were introduced into a round-bottomed flask placed in an ice bath. 16 g of triethylamine were added portionwise to the reaction mixture. After reacting for an additional 3 h, approximately 70 ml of water were added. The aqueous and organic phases were subsequently separated and the organic phase was analysed by GC. The conversion of the 1,1,1,3,3,3-hexafluoroisopropanol was 68%. The yield of ester, based on the amount of 2-fluoroacrylic acid employed in the first stage, was 66%.

Workup

  1. customplaced in an ice bath
  2. customThe aqueous and organic phases were subsequently separated

Sources & evidence

ORD record
ord-c02449b42c1f45c4ba80c9b51c107c04
Source dataset
uspto-grants-2007_12
Patent number
US07304191B2

Reaction notes

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