Water → Benzaldehyde, p-phenylthio-

HRID 1177842Notes

Reaction equation

HRID 1177842 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.O>CN(C=O)C.CCCCCC.CCOC(C)=O>[C:1]1([S:7][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 71023Benzaldehyde, p-phenylthio-Yield 96.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzenethiol (500 mg, 4.537 mmol) was dissolved in 6 mL of DMF. K2CO3 (940 mg, 6.81 mmol) was then added and the resulting mixture was allowed to stir at room temperature for 10 minutes. 4-Fluorobenzaldehyde (675 mg, 5.4 mmol) was then added and the resulting mixture was allowed to stir at 50° C. for 2 hours. The mixture was then stirred at 80° C. for 3 hours. Water was then added and the product was extracted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford a crude product. Purification by column chromatography (using 60-120 mesh silica gel and 5:95: EtOAc:Hexane as the eluent) afforded 940 mg (96% yield) of 4-phenylsulfanyl-benzaldehyde. LC-MS purity: 91.3

Workup

  1. stirringto stir at 50° C. for 2 hours
  2. stirringThe mixture was then stirred at 80° C. for 3 hours
  3. extractionthe product was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford a crude product
  8. customPurification by column chromatography (

Sources & evidence

ORD record
ord-85c1d26e48164899838dea95e63ca10a
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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