Sodium Thiosulfate → tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

HRID 888371Notes

Reaction equation

HRID 888371 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:25]=[C:26]([CH:34]=[C:35]([CH:37]([OH:42])[C:38]([F:41])([F:40])[F:39])[CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:23][C:24]1[CH:25]=[C:26]([CH:34]=[C:35]([C:37](=[O:42])[C:38]([F:40])([F:41])[F:39])[CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59539580Tert-butyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate

Product 1

HCID 68496903tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagant (7.8 g, 18.6 mmol) was added to a solution of tert-Butyl 3-bromo-5-[(R/S)-2,2,2-trifluoro-1-hydroxyethyl]benzoate (4.4 g, 12.4 mmol) in DCM (75 mL). The reaction was stirred for one hour and saturated aq. Na2S2O3 and aq. NaHCO3 were added. The reaction was extracted with DCM (3×) and the organic layers combined and washed with brine, dried over Na2SO4 and concentrated to dryness. Purification using automated flash chromatography (SiO2, 120 g, 0-10% MeOH(NH4OH)/DCM) gave final compound as a mixture of hydrate and ketone which was used directly in step B.

Workup

  1. extractionThe reaction was extracted with DCM (3×)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customPurification

Sources & evidence

ORD record
ord-847f64dcfae7447094af1ac5560175c3
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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