Hydrochloric Acid → 2,2,2-Trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanol

HRID 1499243Notes

Reaction equation

HRID 1499243 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH:17]=[O:18])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Si]([C:23]([F:26])([F:25])[F:24])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[F:24][C:23]([F:26])([F:25])[CH:17]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 1179420475-(Methylsulfonyl)-[1,1'-biphenyl]-2-carbaldehyde

Product 1

HCID 1179420722,2,2-Trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(methylsulfonyl)-[1,1′-biphenyl]-2-carbaldehyde (1 g, 3.8 mmol) was added TMS-CF3 (1.0 g, 7.7 mmol) in THF (10 mL). The reaction was cooled to 0° C. to and TBAF (0.57 mL, 0.57 mmol) was added dropwise. The reaction mixture was stirred for 2 h, then 3 N HCl (2 mL) was added to the mixture and the reaction mixture was stirred for an additional 30 min. The mixture was extracted with ethyl acetate, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification on normal phase silica gel provided 2,2,2-trifluoro-1-(5-(methylsulfonyl)-[1,1′-biphenyl]-2-yl)ethanol as a white solid.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred for an additional 30 min
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification on normal phase silica gel

Sources & evidence

ORD record
ord-7b33c1f66295430f817ced423edd0e43
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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