3-Chlorophenol → 2-Bromo-5-chlorophenol

HRID 1815831Notes

Reaction equation

HRID 1815831 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Br:9]Br>ClCCl.O>[Br:9][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[OH:8]

Participants

5

Reactant 2

HCID 79333-ChlorophenolHCID 24408Bromine

Product 1

HCID 132842722-Bromo-5-chlorophenolYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.03 gm (39.1 mMol) 3-chlorophenol in 20 mL dichloromethane was cooled in an ice bath as 6.25 gm (39.1 mMol) bromine were added dropwise. The reaction mixture was allowed to warm to room temperature and was stirred for 16 hours. The reaction mixture was diluted with water, the phases separated, and the organic phase dried over magnesium sulfate. The residue was subjected to silica gel chromatography, eluting with 3:2 dichloromethane:hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 2.04 gm (25%) of 2-bromo-5-chlorophenol.

Workup

  1. additionwere added dropwise
  2. customthe phases separated
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. washeluting with 3:2 dichloromethane
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfb8896c94b641cabdb8486ab90ad156
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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