Cesium carbonate → 4-(4-Hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

HRID 605348Notes

Reaction equation

HRID 605348 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[SH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2401474-MercaptophenolHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 668084784-(4-Hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-chloro-3-nitrobenzoic acid methyl ester (4.00 g, 18 mmol) and 4-mercaptophenol (2.37 g, 18 mmol) in acetone (60 mL) was added Cs2CO3 (5.93 g, 18 mmol) at room temperature, and then the mixture was refluxed for 30 minutes. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated. The residue was diluted with AcOEt (30 mL), washed with H2O (3 times) and brine, dried over MgSO4, and evaporated to give brown oil. The oily residue was separated by silica gel column chromatography (n-hexane/AcOEt=4/3) to give the title compound as yellow amorphous (5.60 g).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated
  4. additionThe residue was diluted with AcOEt (30 mL)
  5. washwashed with H2O (3 times) and brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give brown oil
  9. customThe oily residue was separated by silica gel column chromatography (n-hexane/AcOEt=4/3)

Sources & evidence

ORD record
ord-73230ab517004cdf96b6709bae134bd6
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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