Sodium Thiosulfate → 3-Fluoro-5-(methanesulfonyl)benzaldehyde

HRID 1675141Notes

Reaction equation

HRID 1675141 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[F:23][C:24]1[CH:25]=[C:26]([CH2:34][OH:35])[CH:27]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:29]=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([CH:27]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:29]=1)[CH:34]=[O:35]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67341497HCID 67341497, compound

Product 1

HCID 576525233-Fluoro-5-(methanesulfonyl)benzaldehydeYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (530 mg, 1.21 mmol) was added in one portion to [3-fluoro-5-(methylsulfonyl)phenyl]methanol (225 mg, 1.10 mmol) in DCM (20 mL) at 22° C. The resulting solution was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with DCM (50 ml) and poured into saturated aqueous sodium bicarbonate (30 mL) containing sodium thiosulfate (1219 mg, 7.71 mmol). The resulting suspension was stirred for 10 minutes before separating the layers. The organic layer was washed with water (1×50 mL), dried over MgSO4 and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 30 to 40% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 3-fluoro-5-(methylsulfonyl)benzaldehyde (168 mg, 75%) as a white solid.

Workup

  1. stirringThe resulting suspension was stirred for 10 minutes
  2. custombefore separating the layers
  3. washThe organic layer was washed with water (1×50 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified by flash silica chromatography, elution gradient 30 to 40% EtOAc in isohexane
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-0893519ca1e2483287989335e7dd4b02
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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