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

HRID 2358545Notes

Reaction equation

HRID 2358545 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 4a (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-2c18d28d9c644501bff2218d695dbaa0
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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