Hydrochloric Acid → 1-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanol

HRID 1620855Notes

Reaction equation

HRID 1620855 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[C:22]([F:28])[CH:21]=1.[Si]([C:33]([F:36])([F:35])[F:34])(C)(C)C.Cl>C1COCC1>[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]([OH:25])[C:33]([F:36])([F:35])[F:34])=[C:22]([F:28])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 616446351-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.1 ml) was added to a solution of 4-bromo-2-fluoro-benzaldehyde (2.03 g, 10 mmol) and TMSCF3 (20 ml, 12 mmol) in 10 ml THF at 0° C. The formed mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was then treated with 12 ml of 3M HCl and stirred overnight. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 2.4g of 1-(4-bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanol (yield: 90%).

Workup

  1. stirringstirred overnight
  2. extractionThe product was extracted with ethyl acetate (3×20 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-be8153c294e24ae2bb4c8f12ae2b7729
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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