Bromine → 4-Bromo-2,6-difluorophenol

HRID 2078401Notes

Reaction equation

HRID 2078401 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[OH:11]>C(O)(=O)C>[Br:1][C:8]1[CH:9]=[C:4]([F:3])[C:5]([OH:11])=[C:6]([F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 943922,6-Difluorophenol

Product 1

HCID 27362924-Bromo-2,6-difluorophenolYield 118.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (13.54 g, 0.0846 mol) dissolved in acetic acid (40 mL) was added drop by drop to a cooled solution of 2,6-difluorophenol (20 g, 0.153 mol) in acetic acid (80 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with saturated aqueous sodium bisulfite solution and then extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure afforded 4-bromo-2,6-difluorophenol (21 g) as a yellow liquid. This was employed directly in the next step without further purification.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium bisulfite solution
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-f99f5d90ade8427999d9a9ea1a7788d1
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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