Bromine → 2-Bromo-3,5-difluorophenol

HRID 1815832Notes

Reaction equation

HRID 1815832 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[Br:10]Br>C(=S)=S.C(OCC)C>[Br:10][C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[OH:9]

Participants

5

Reactant 2

HCID 24408BromineHCID 759283,5-Difluorophenol

Product 1

HCID 221448602-Bromo-3,5-difluorophenolYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6348Carbon DisulfideSolvent2×

Procedure

A solution of 2.6 gm (20 mMol) 3,5-difluorophenol in 20 mL carbon disulfide was cooled to 0° C. and then a solution of 1.02 mL (20 mMol) bromine in 10 mL carbon disulfide was added dropwise over 30 minutes. After stirring for an additional 30 minutes, the reaction mixture was warmed to room temperature and stirred for 1.5 hours. The reaction mixture was diluted with 200 mL diethyl ether and was washed sequentially with aqueous sodium metabisulfite and saturated aqueous sodium chloride. The organic phase was then dried over sodium sulfate and concentrated under reduced pressure. The residue was vacuum distilled to provide 2.5 gm (60%) of 2-bromo-3,5-difluorophenol (b.p.=65° C. (5 mm Hg)).

Workup

  1. stirringstirred for 1.5 hours
  2. washwas washed sequentially with aqueous sodium metabisulfite and saturated aqueous sodium chloride
  3. dry with materialThe organic phase was then dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationdistilled

Sources & evidence

ORD record
ord-c40255f429134ed694c52d15f97a4f9c
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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