Hydrogen Peroxide → 2,3-Difluoro-4-octoxy-4'-hydroxybiphenyl

HRID 343257Notes

Reaction equation

HRID 343257 reaction equation
[OH:1]O.[F:3][C:4]1[C:9]([F:10])=[C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:7]=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>C(OCC)C>[F:3][C:4]1[C:9]([F:10])=[C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:7]=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][C:23]([OH:1])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 106899942,3-Difluoro-4-octoxybiphenyl-4'-yl-boronic acid

Product 1

HCID 105687302,3-Difluoro-4-octoxy-4'-hydroxybiphenyl

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10% hydrogen peroxide (10.5 ml, 0.023 mol) was added dropwise to a stirred, refluxing solution of 2,3 -difluoro-4 -octoxybiphenyl-4'-yl-boronic acid (10) (2.9g, 8.0 mmol), in diethyl ether (40 ml). The stirred mixture was heated under reflux until tic showed the reaction to be complete. The ether layer was separated and the aqueous layer extracted with ether. The combined ethereal layers were washed with water and dried. The solvent was removed. The crude product was purified by flash chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 2:1) to give a white solid which was recrystallised from pentane/ethyl acetate mixtures.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux
  3. customthe reaction
  4. customThe ether layer was separated
  5. extractionthe aqueous layer extracted with ether
  6. washThe combined ethereal layers were washed with water
  7. customdried
  8. customThe solvent was removed
  9. customThe crude product was purified by flash chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 2:1)
  10. customto give a white solid which
  11. customwas recrystallised from pentane/ethyl acetate mixtures

Sources & evidence

ORD record
ord-95f790615b124a62bcd85febcbb96f8a
Source dataset
uspto-grants-1999_01
Patent number
US05861109

Reaction notes

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