Trifluoroacetic acid methylene chloride → HCID 11710738, compound

HRID 1452695Notes

Reaction equation

HRID 1452695 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:24]CC2C=CC(OC)=CC=2)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[Cl:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:16]([F:17])([F:18])[F:19])[C:20]([F:22])([F:23])[F:21])=[CH:11][C:10]=1[Cl:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86604223HCID 86604223, compound

Product 1

HCID 11710738HCID 11710738, compoundYield 12%

Procedure

82 mg (0.2 mmol) of crude 1-benzyloxy-2-chloro-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-benzene were treated with 3 mL of a mixture of dichloromethane/trifluoroacetic acid (1:3) at room temperature for 1 h. The solvent was evaporated and the residue was redissolved in a mixture of diethyl ether and a solution of Na2CO3. The inorganic phase was extracted with diethyl ether and the combined organic phases were washed with brine and dried (Na2SO4). After filtration and evaporation of the solvent, the crude product was purified by column chromatography to give 7.3 mg (12%) of 2-(4-benzyloxy-3-chloro-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol as a yellow gum, MS: 383 (M−H, 1Cl)−.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was redissolved in a mixture of diethyl ether
  3. extractionThe inorganic phase was extracted with diethyl ether
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationAfter filtration and evaporation of the solvent
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-65c26d97a48b46168ff4fd7c3b28ac17
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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