Hydrochloric Acid → 1-(3,4-Difluorophenyl)-2,2,2-trifluoroethanol

HRID 559093Notes

Reaction equation

HRID 559093 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH:23]=[O:24].[F:29][C:30]([Si](C)(C)C)([F:32])[F:31].Cl>C1COCC1>[F:19][C:20]1[CH:21]=[C:22]([CH:23]([OH:24])[C:30]([F:32])([F:31])[F:29])[CH:25]=[CH:26][C:27]=1[F:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 5880883,4-DifluorobenzaldehydeHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 610879271-(3,4-Difluorophenyl)-2,2,2-trifluoroethanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (TBAF: 0.1 ml, 1M) in THF was added to a solution of 3,4-difluoro-benzaldehyde (1.42 g, 10 mmol) and (trifluoromethyl)trimethylsilane (1.70 g, 12 mmol) in 10 ml THF at 0° C. The mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was treated with 12 ml of 1M HCl and stirred overnight. The product was extracted with dichloromethane (3×20 ml), the organic layer was combined and passed through a pad of silica gel. The organic solvent was evaporated to give 1.9 g of 1-(3,4-difluoro-phenyl)-2,2,2-trifluoro-ethanol, yield 90%.

Workup

  1. stirringstirred overnight
  2. extractionThe product was extracted with dichloromethane (3×20 ml)
  3. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-5622981b0923441fa5e41980bb1ad662
Source dataset
uspto-grants-2011_11
Patent number
US08063057B2

Reaction notes

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