3,4-Dichlorophenol → HCID 13078524, compound

HRID 2164629Notes

Reaction equation

HRID 2164629 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[CH:16][C:17]=1[Cl:18].C([O-])([O-])=O.[K+].[K+].S1(CCCC1)(=O)=O.[OH-].[Na+]>O>[Cl:18][C:17]1[CH:16]=[CH:15][C:14]([O:19][C:7]2[CH:8]=[CH:9][C:4]([S:2]([CH3:1])=[O:3])=[CH:5][CH:6]=2)=[CH:13][C:12]=1[Cl:11]

Participants

7

Reactant 5

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 31347SulfolaneHCID 53241841-fluoro-4-methanesulfinylbenzene

Product 1

HCID 13078524HCID 13078524, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 16.14 g (0.102 mole) of 4-fluorophenyl methyl sulfoxide, 33.18 g (0.204 mole) of 3,4-dichlorophenol, 28.15 g (0.204 mole) of anhydrous K2CO3 and 150 ml of sulfolane was heated at 170° C. for 4 hrs and cooled. The reaction mixture was poured into a solution of 20% aqueous NaOH and 500 ml of water. The homogeneous solution was extracted with diethyl ether. The organic layer was washed with water, dried (Na2SO4) and solvent removed in vacuo leaving 24.5 g (79.8% yield) of product. Recrystallization from ethanol followed by column chromatography using silica gel as the support and chloroform as the eluent afforded purified 1,2-dichloro-4-(4-(methylsulfinyl)phenoxy)benzene, mp 92°-93.5° C.

Workup

  1. temperaturecooled
  2. extractionThe homogeneous solution was extracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4) and solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-9bb28b33671c4377b3163651613577ad
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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