Methylparaben → 4-(3-Methanesulfonyl-phenoxy)-benzoic acid methyl ester

HRID 552580Notes

Reaction equation

HRID 552580 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=1.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([O:21][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 62657Potassium Phosphate, TribasicHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-2×

Product 1

HCID 671652314-(3-Methanesulfonyl-phenoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

1-Bromo-3-methanesulfonyl-benzene (11.0 mmol) (see Intermediate 11) and 4-hydroxy-benzoic acid methyl ester (1.2 mmol) are dissolved in toluene (0.1M). Palladium acetate (0.02 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (0.03 mmol) and tri-basic potassium phosphate (2.0 mmol) are added and the reaction heated reaction at 90° C. for 18 h. The reaction is allowed to cool to room temperature, washed with water while and then the aqueous extracted with dichloromethane. The organic portions are combined and concentrated in vacuo and purified by radial silica chromatography, eluting with ethyl acetate and hexane.

Workup

  1. temperaturethe reaction heated
  2. customreaction at 90° C. for 18 h
  3. washwashed with water while and then the
  4. extractionaqueous extracted with dichloromethane
  5. concentrationconcentrated in vacuo
  6. custompurified by radial silica chromatography
  7. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-59e45b144b3942faa4942252285d6886
Source dataset
uspto-grants-2011_05
Patent number
US07951826B2

Reaction notes

Loading…