Hydrochloric Acid → 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran

HRID 1282417Notes

Reaction equation

HRID 1282417 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1/[CH:12]=[CH:13]\[C:14]([CH2:18][F:19])([OH:17])[CH2:15][F:16].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[F:16][CH2:15][C:14]1([CH2:18][F:19])[CH:13]=[CH:12][C:3]2[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=2[O:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 86587552HCID 86587552, compound

Product 1

HCID 184244212,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyranYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(2-chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-cis-buten-2-ol (8.80 g), potassium tert-butoxide (3.50 g) and N,N-dimethylformamide (60 ml) was stirred at 60° C. for 40 minutes. To the reaction mixture, 2 N HCl was added, followed by extraction with ethyl acetate; the resulting organic layers were combined, washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 2,2-bis(fluoromethyl)-6-trifluoromethyl-2H-1-benzopyran (7.0 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d485e3ae33b4120857d480089273a93
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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