Hydrochloric Acid → 2,2,2-Trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethanol

HRID 1629758Notes

Reaction equation

HRID 1629758 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.C[Si](C)(C)[C:19]([F:22])([F:21])[F:20].Cl>COCCOC.CCOC(C)=O.[F-].[Cs+]>[F:20][C:19]([F:22])([F:21])[CH:11]([C:10]1[CH:13]=[CH:14][C:7]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:15])([F:16])[F:1])=[CH:8][CH:9]=1)[OH:12]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 53724788HCID 53724788, compound

Product 1

HCID 866858472,2,2-Trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethanolYield 123.4%

Reagents, catalysts & solvents 3

HCID 25953Cesium fluorideCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of Intermediate 2A (26.7 g, 114 mmol) and trimethyl(trifluoromethyl)silane (16.9 g, 119 mmol) in anhydrous DME (112 mL) was added CsF (500 mg, 3.29 mmol). The reaction was stirred at rt for 16 h. To the mixture was added 4 N aq HCl (114 mL) and the reaction was stirred at rt for 2.5 h. The reaction was diluted with EtOAc (300 mL) and washed with water, sat'd aq NaHCO3, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide Intermediate 2B (42.5 g, 122%) as an oil. The crude product was used without further purification. LCMS Anal. Calc'd for C12H12F6O2 302.21, found [M−H] 301.2.

Workup

  1. stirringthe reaction was stirred at rt for 2.5 h
  2. washwashed with water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-990dedffbd184b71894588ed0b152300
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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