Sodium Thiosulfate → 1-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

HRID 1400010Notes

Reaction equation

HRID 1400010 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([OH:35])[C:31]([F:34])([F:33])[F:32])=[C:26]([F:36])[CH:25]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[C:26]([F:36])[CH:25]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 616446351-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanol

Product 1

HCID 669578641-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethan-1-oneYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (16.57 g, 39.06 mmol) was added to a solution of 1-(4-bromo-2-fluoro-phenyl)-2,2,2-trifluoro-ethanol (10.66 g, 39.06 mmol) in DCM (100 mL) and the reaction mixture was stirred at rt for 1.5 h. Na2S2O3 (10% aq., 100 mL) was added and the resulting mixture extracted with CH2Cl2 (100 mL). The organic layer was washed with Na2S2O3 (50 mL×2), NaHCO3 (satd. aq., 100 mL×2), and brine (100 mL×2). The organic layers were dried (Na2SO4) and concentrated. The crude material was purified (FCC) to yield the title compound (3.20 g, 30%).

Workup

  1. extractionthe resulting mixture extracted with CH2Cl2 (100 mL)
  2. washThe organic layer was washed with Na2S2O3 (50 mL×2), NaHCO3 (satd. aq., 100 mL×2), and brine (100 mL×2)
  3. dry with materialThe organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude material was purified (FCC)

Sources & evidence

ORD record
ord-064ecf751850458781551230dc498f8f
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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