Hydrochloric Acid → 2-(Trifluoromethyl)acrylic acid

HRID 1380412Notes

Reaction equation

HRID 1380412 reaction equation
BrC([C:4]([F:7])([F:6])[F:5])=C.[OH2:8].C(N([CH2:14][CH3:15])CC)C.Cl.[O:17]1[CH2:21]CCC1>>[F:5][C:4]([F:7])([F:6])[C:14](=[CH2:15])[C:21]([OH:17])=[O:8]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-

Product 1

HCID 5876942-(Trifluoromethyl)acrylic acidYield 67%

Procedure

A mixture of dichlorobis(triphenylphosphine) palladium (5.5 g; 7.85×10-3 mole), 2-bromo-3,3,3-trifluoropropene (139 g; 0.794 mole), water (20 g; 1.11 moles) and triethylamine (109 g; 1.08 moles) in tetrahydrofuran (500 ml) was put in a one-liter stainless steel autoclave, and heated at 75° to 80° C. with stirring for 2 hours under a carbon monoxide pressure of 35 atmospheres. 2N-Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with diethyl ether and then dried over anhydrous sodium sulfate. Distillation of the extract under reduced pressure gave 74.1 g (yield: 67%) of α-trifluoromethylacrylic acid having a boiling point of 90°/28 mmHg. m.p.: 52.5°-53.0° C.

Workup

  1. temperatureheated at 75° to 80° C.
  2. extractionthe mixture was extracted with diethyl ether
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationDistillation of the
  5. extractionextract under reduced pressure

Sources & evidence

ORD record
ord-39d7319dd50a49ffaad3499604280be3
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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