Potassium Acetate → 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid

HRID 397023Notes

Reaction equation

HRID 397023 reaction equation
[C]=O.[F:3][CH2:4][C:5]1([CH2:27][F:28])[CH:10]=[C:9](OS(C(F)(F)F)(=O)=O)[C:8]2[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:7]=2[O:6]1.[C:29]([O-:32])(=[O:31])C.[K+]>CN(C)C(=O)C>[F:3][CH2:4][C:5]1([CH2:27][F:28])[CH:10]=[C:9]([C:29]([OH:32])=[O:31])[C:8]2[CH:19]=[C:20]([C:23]([F:24])([F:25])[F:26])[CH:21]=[CH:22][C:7]=2[O:6]1

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 12070531trifluoromethanesulfonic acid 2,2-bis(fluoromethyl)-6-(trifluoromethyl)-2H-1-benzopyran-4-yl esterHCID 178418416HCID 178418416, compound

Product 1

HCID 98796402,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A three-necked 50-ml flask (equipped with a reflux condenser, a thermometer, and a CO introducing pipe connected with a balloon charged with carbon monoxide gas) was charged with 1.0 g (2.4 mmol) of trifluoromethanesulfonic acid 2,2-bis(fluoromethyl)-6-(trifluoromethyl) -2 H- 1-benzopyran-4-yl ester, 0.95 g (9.7 mmol) of potassium acetate, and 10 ml of N,N-dimethylacetamide. Under stirring of the mixture, predetermined amounts of reagents were added, as shown in Table. Then, the reaction was conducted under conditions shown in Table. After that, the reaction mixture was subjected to the same post-treatments as those of Example 5. As a result, 2,2-bis(fluoromethyl)-6-(trifluoromethyl)-2 H- 1-benzopyran-4-carboxylic acid was obtained, as shown by yield in Table.

Workup

  1. customA three-necked 50-ml flask (equipped with a reflux condenser
  2. additionwere added

Sources & evidence

ORD record
ord-b3fa476485b843eb8e67422a2e199b84
Source dataset
uspto-grants-2003_08
Patent number
US06608217B2

Reaction notes

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