Water → 4-(4-Methoxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

HRID 605166Notes

Reaction equation

HRID 605166 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[CH3:10][O:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16](Cl)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1.O>CN(C=O)C>[CH3:10][O:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([S:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 127654-MethoxybenzenethiolHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 41664294-(4-Methoxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-methoxy thiophenol (5 mL, 40.7 mmol) and methyl-3-nitro-4-chlorobenzoate (10.52 g, 48.8 mmol) in DMF (40 mL) was added CsCO3 (26.5 g, 81.4 mmol) and the reaction mixture heated at 80° C. for 3 hours. After cooling, the solution was poured into water and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum to afford the title compound after chromatography on silica gel using ethyl acetate/hexanes as eluent (10.93 g, 80%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9e225d67bc784edd9689f2137d095bcb
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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