Bromine → 4-Bromo-2,5-difluorophenol

HRID 2387277Notes

Reaction equation

HRID 2387277 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[Br:10]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:10][C:6]1[C:5]([F:8])=[CH:4][C:3]([OH:9])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 949522,5-Difluorophenol

Product 1

HCID 70180424-Bromo-2,5-difluorophenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2,5-difluorophenol (40, 5.50 g, 0.0423 mol) in chloroform (110.0 mL), bromine (2.18 mL, 0.0423 mol) was added slowly. After 3 hours, the reaction was poured into a solution of sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified with silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a colorless oil (41, 6.20 g, 70.2%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 20% ethyl acetate in hexane
  6. customto give a colorless oil (41, 6.20 g, 70.2%)

Sources & evidence

ORD record
ord-d5f00babb3e8494a96e010f8d5914940
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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