2-Fluorophenol → 4-Bromo-2-fluorophenol

HRID 1992361Notes

Reaction equation

HRID 1992361 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) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with aq. sodium bisulfite solution and 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-fluorophenol (210 g) as a liquid. This was directly taken for next step without further purification.

Workup

  1. customThe reaction mixture was quenched with aq. 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-ecb0b32e91114f5faedf4c586a400648
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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