Sodium Carbonate → 4-(4-Methyl-2-nitro-phenylsulfanyl)-phenol

HRID 607146Notes

Reaction equation

HRID 607146 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[SH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2401474-MercaptophenolHCID 713468894-Methyl-2-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 549110984-(4-Methyl-2-nitro-phenylsulfanyl)-phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 6a (11.22 g, 39.3 mmol) and 4-mercaptophenol (4.96 g, 39.3 mmol) in 100 mL of EtOH was treated with Na2CO3 and heated overnight under efflux. Cooled to room temperature and quenched with water. Extracted with EtOAc. Dried over MgSO4, filtered and concentrated under vacuum giving the title compound, which was purified by silica gel column chromatography eluting with 25% EtOAc/hexane giving a red oil (8.65 g, 85%).

Workup

  1. temperatureheated overnight under efflux
  2. customquenched with water
  3. extractionExtracted with EtOAc
  4. dry with materialDried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f9ede5f1ff4f4da8af69b90107b41d7e
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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