2,4-Dichlorophenol → 2-Bromo-4,6-dichlorophenol

HRID 2100357Notes

Reaction equation

HRID 2100357 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C>[Br:15][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 206172-Bromo-4,6-dichlorophenolYield 92.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,4-dichlorophenol (4 g, 24.5 mmol) and sodium acetate (2 g, 24.5 mmol) in acetic acid (40 ml) was added bromine (1.3 ml, 24.5 mmol) and the reaction stirred at room temperature for 14 hours. The reaction was poured into 600 ml ice and filtered. The product was extracted into dichloromethane (200 ml) dried over sodium sulphate and concentrated in vacuo to furnish 5.5 g of the title product as a yellow solid.

Workup

  1. filtrationfiltered
  2. extractionThe product was extracted into dichloromethane (200 ml)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-002ca3759f664801ac5f96f054849878
Source dataset
uspto-grants-2009_08
Patent number
US07572797B2

Reaction notes

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