4-Bromotoluene → 1-(4'-Chlorobiphenyl-4-yloxy)-4-methylbenzene

HRID 1253227Notes

Reaction equation

HRID 1253227 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.Br[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1.[OH-].[K+]>CO.[Cu].O.CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

9

Reactant 4

HCID 78054-BromotolueneHCID 14797Potassium HydroxideHCID 915894'-Chloro-4-biphenylolHCID 23665647Potassium tert-butoxide

Product 1

HCID 138853171-(4'-Chlorobiphenyl-4-yloxy)-4-methylbenzeneYield 29%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

Potassium t-butoxide (20 g) was added to a solution of 4-chloro-4'-hydroxybiphenyl (mp 142° C., prepared as in J.A.C.S, 2219, 1964) (33 g) in methanol (200 ml). The resulting mixture was evaporated to dryness under reduced pressure and the solid residue obtained was mixed with p-bromotoluene (83 g), copper powder (1 g) and dimethylsulphoxide (80 ml). The resulting mixture was refluxed (190° C.) for 16 hours, potassium hydroxide (9 g) was added and the mixture was refluxed for a further 6 hours. After cooling, the mixture was poured into water and extracted with methylene chloride. The methylene chloride extract was washed with water, dried (MgSO4) and evaporated to give a crude product in the form of an oil which solidified on standing. This crude product was triturated with 60/80 petroleum ether to give 1-(4'-chlorobiphenyl-4-yloxy)-4-methylbenzene (10 g, 29%) mp 130° C.

Workup

  1. customThe resulting mixture was evaporated to dryness under reduced pressure
  2. customthe solid residue obtained
  3. temperaturethe mixture was refluxed for a further 6 hours
  4. temperatureAfter cooling
  5. extractionextracted with methylene chloride
  6. extractionThe methylene chloride extract
  7. washwas washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a crude product in the form of an oil which
  11. customThis crude product was triturated with 60/80 petroleum ether

Sources & evidence

ORD record
ord-cb78f14989ff49e7b0583f1a9bafde5c
Source dataset
uspto-grants-1988_05
Patent number
US04748185

Reaction notes

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