Trimethyl borate → 4-Ethoxy-2,3-difluorophenol

HRID 1534273Notes

Reaction equation

HRID 1534273 reaction equation
F[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9]C=[C:7]([F:11])[CH:6]=1.[F:12]C1C(F)=CC=CC=1C1C=CC(OCCCCCCC)=CC=1.B([O:39][CH3:40])(OC)OC.OO.O>C(O)(=O)C>[CH2:3]([O:4][C:5]1[CH:10]=[CH:9][C:40]([OH:39])=[C:7]([F:11])[C:6]=1[F:12])[CH3:2]

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 449047Hydrogen peroxide waterHCID 150586222,3-Difluoro-1-ethoxybenzeneHCID 191036002,3-Difluoro-4'-heptyloxybiphenyl

Product 1

HCID 144957634-Ethoxy-2,3-difluorophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.02 mol of 2,3-difluoroethoxybenzene are metalated according to 1b. Subsequently, 0.02 mol of trimethyl borate are added dropwise at a temperature of about -55° to -60° C. during the course of 0.5 h. The resulting suspension is subsequently stirred for a further 0.5 h, the temperature climbing to about -20°. 1.5 ml of 98% acetic acid are added. After about 15 min, the mixture is cooled to about -35° and a solution of 30% H2O2 /H2O (5 ml/2 ml) is added dropwise. After stirring for 2 h while slowly warming to room temperature, the organic phase is separated and the aqueous phase is extracted with methyl tert.butyl ether. Finally, the mixture is washed with saturated NaCl solution, dried and evaporated.

Workup

  1. customclimbing to about -20°
  2. waitAfter about 15 min
  3. temperaturethe mixture is cooled to about -35°
  4. stirringAfter stirring for 2 h
  5. customthe organic phase is separated
  6. extractionthe aqueous phase is extracted with methyl tert.butyl ether
  7. washFinally, the mixture is washed with saturated NaCl solution
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-7973b3cf5f30402f8ebe99e188c1035f
Source dataset
uspto-grants-1992_02
Patent number
US05087764

Reaction notes

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