Trichloroethanol → 2,2,2-Trichloroethyl-2-fluoroacrylate

HRID 968982Notes

Reaction equation

HRID 968982 reaction equation
[F:1][C:2](=[CH2:6])[C:3](Cl)=[O:4].[Cl:7][C:8]([Cl:12])([Cl:11])[CH2:9][OH:10].C(N(CC)CC)C>O>[F:1][C:2](=[CH2:6])[C:3]([O:10][CH2:9][C:8]([Cl:12])([Cl:11])[Cl:7])=[O:4]

Participants

5

Reactant 3

HCID 8259TrichloroethanolHCID 8471TriethylamineHCID 27833352-Fluoroacryloyl chloride

Product 1

HCID 27825302,2,2-Trichloroethyl-2-fluoroacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12 g of 2-fluoroacryloyl chloride and 26 g of 2,2,2-trichloroethanol were introduced into a round-bottomed flask placed in an ice bath. 17 g of triethylamine were added portionwise to the reaction mixture. After reacting for an additional 3 h, approximately 50 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 2,2,2-trichloroethanol was 52%. The yield of ester, based on the amount of 2-fluoroacrylic acid employed in the first stage, was 67%.

Workup

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

Sources & evidence

ORD record
ord-d4d39609322f436bbc68b8ba4785752a
Source dataset
uspto-grants-2007_12
Patent number
US07304191B2

Reaction notes

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