Hydrochloric Acid → 4'-Ethoxy-2,3,2',3'-tetrafluorobiphenyl-4-ol

HRID 2262357Notes

Reaction equation

HRID 2262357 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[C:6]([F:13])[C:5]=1[F:14])[CH3:2].Br[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[C:17]=1[F:24].C(=O)([O-])[O-].[Na+].[Na+].Cl>[Pd].CC(O)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[C:17]=2[F:24])=[C:6]([F:13])[C:5]=1[F:14])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 102199424-Bromo-2,3-difluorophenolHCID 15135235B-(4-Ethoxy-2,3-difluorophenyl)boronic acid

Product 1

HCID 579529364'-Ethoxy-2,3,2',3'-tetrafluorobiphenyl-4-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

In a reactor under nitrogen atmosphere, 20.0 g of compound (a2)17.2 g of 4-bromo-2,3-difluorophenol (a3), 30.6 g of sodium carbonate, 0.54 g of palladium on carbon catalyst (Pd/C) were dissolved in 120 mL of 2-propanol (IPA). After stirring by refluxing for 10 hours, the reaction mixture was cooled to room temperature, and injected into a mixture of 500 ml of 1N hydrochloric acid and 300 ml of toluene which was cooled into 0° C. The mixture was separated into organic layer and aqueous layer and the organic layer was extracted. The resulting organic layer was washed with saturated chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to provide the residue. The resulting residue was purified by recrystallization from heptan, dried to provide 13.2 g of 4′-ethoxy-2,3,2′,3′-tetrafluorobiphenyl-4-ol (a4) as a white solid.

Workup

  1. temperatureby refluxing for 10 hours
  2. temperaturewas cooled into 0° C
  3. customThe mixture was separated into organic layer and aqueous layer
  4. extractionthe organic layer was extracted
  5. washThe resulting organic layer was washed with saturated chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customto provide the residue
  9. customThe resulting residue was purified by recrystallization from heptan
  10. customdried

Sources & evidence

ORD record
ord-a0cc6fa911fe4f5f8aeeff61e4ae2ea0
Source dataset
uspto-grants-2010_12
Patent number
US07851032B2

Reaction notes

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