Trifluoroacetic acid → 2,4-Difluoro-3-vinylbenzoic acid

HRID 658096Notes

Reaction equation

HRID 658096 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:21]([CH:22]=[CH2:23])=[C:20]([F:24])[CH:19]=[CH:18][C:10]=1[C:11]([O:13]C(C)(C)C)=[O:12]>ClCCl>[F:8][C:9]1[C:21]([CH:22]=[CH2:23])=[C:20]([F:24])[CH:19]=[CH:18][C:10]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68451303HCID 68451303, compound

Product 1

HCID 684536492,4-Difluoro-3-vinylbenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4.27 ml portion of trifluoroacetic acid was added to 30 ml of dichloromethane solution containing 1.33 g of tert-butyl 2,4-difluoro-3-vinylbenzoate and stirred for 5 hours. After evaporation of the solvent, appropriate amounts of purified water and saturated sodium bicarbonate aqueous solution were added thereto and the water layer was washed with diethyl ether. The water layer was adjusted to pH 1 with 1 M hydrochloric acid aqueous solution, extracted with diethyl ether and then dried with anhydrous magnesium sulfate. After concentration, 964 mg (95%) of 2,4-difluoro-3-vinylbenzoic acid (Reference Example 6-1) was obtained.

Workup

  1. customAfter evaporation of the solvent, appropriate amounts of purified water and saturated sodium bicarbonate aqueous solution
  2. additionwere added
  3. washthe water layer was washed with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationAfter concentration

Sources & evidence

ORD record
ord-dee5542b17c24c0abc972d8d95cbaa24
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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