Thiophenol → 1-Methyl-2-nitro-4-(phenylthio)benzene

HRID 2390195Notes

Reaction equation

HRID 2390195 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 565939751-Methyl-2-nitro-4-(phenylthio)benzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-fluoro-2-nitrotoluene (ABCR; 120 μl; 0.97 mmol), thiophenol (120 μl; 1.16 mmol) and K2CO3 (267 mg; 1.93 mmol) in DMSO (3 ml) was placed in a microwave vial and submitted to microwave irradiation at 150° C. for 15 minutes. The reaction mixture was filtered, taken up in EtOAc and washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc affording the title compound as a yellow solid.

Workup

  1. customirradiation at 150° C. for 15 minutes
  2. filtrationThe reaction mixture was filtered
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica)
  8. washeluting with cyclohexane containing
  9. temperatureincreasing amounts of EtOAc affording the title compound as a yellow solid

Sources & evidence

ORD record
ord-75084fa1a6454c92a836091614a4ae9f
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…