2-Fluorophenol → 4-Bromo-2-fluorophenol

HRID 2078408Notes

Reaction equation

HRID 2078408 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10]>C(O)(=O)C>[Br:1][C:8]1[CH:7]=[CH:6][C:5]([OH:10])=[C:4]([F:3])[CH:9]=1

Participants

4

Reactant 2

HCID 97072-FluorophenolHCID 24408Bromine

Product 1

HCID 27249814-Bromo-2-fluorophenolYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (68.7 mL, 1.339 mol) dissolved in acetic acid (300 mL) was added drop by drop to a cooled solution of 2-fluorophenol (150 g, 1.339 mol) in acetic acid (1300 mL). The resulting mixture was stirred at room temperature overnight before being quenched with aqueous sodium bisulfite solution and extracted with dichloromethane. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure afforded 4-bromo-2-fluorophenol (210 g) as a liquid. This was employed directly in the next step without further purification.

Workup

  1. custombefore being quenched with 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-ee2cfc0128bc4c08bdedde8b1abaf891
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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