Phenol → 4-Bromo-1-chloro-2-(phenoxymethyl)benzene

HRID 2265795Notes

Reaction equation

HRID 2265795 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH2:22]Br)[CH:16]=1>C(O)C>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH2:22][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzene

Product 1

HCID 115149114-Bromo-1-chloro-2-(phenoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of phenol (7.1 g) and potassium carbonate (11.1 g) in ethanol (100 mL) is added 4-bromo-2-bromomethyl-1-chloro-benzene (19.5 g). The mixture is stirred at ambient temperature over night. The ethanol is evaporated, and water is added to the residue. The resulting mixture is extracted with ethyl acetate, the combined extracts are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 70:30).

Workup

  1. customThe ethanol is evaporated
  2. additionwater is added to the residue
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. dry with materialthe combined extracts are dried over sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 70:30)

Sources & evidence

ORD record
ord-2d2312a1094849d9a17e618f3c44b163
Source dataset
uspto-grants-2010_12
Patent number
US07858587B2

Reaction notes

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