Water → 2-(Benzyloxy)-1-bromo-3,5-difluorobenzene

HRID 451700Notes

Reaction equation

HRID 451700 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1.[OH-].[K+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1COCC1>[CH2:17]([O:10][C:3]1[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 27362902-Bromo-4,6-difluorophenol

Product 1

HCID 467393982-(Benzyloxy)-1-bromo-3,5-difluorobenzeneYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
64 °C

Procedure

2-Bromo-4,6-difluoro-phenol (10 g, 48 mmol), Bu4NBr (0.24 g, 0.72 mol) and BnBr (8.22 g, 48 mmol) was mixed in THF (100 mL). 50% KOH (13.46 g, 240 mmol) was added to the mixture, heated to 64° C. and stirred for 2 h. Water was added to the mixture, the aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product 2-(benzyloxy)-1-bromo-3,5-difluorobenzene (13.7 g, 96%), which was used immediately without purification.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcd84c1e2a634e4498fcffdf2a6188a7
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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