Phenol → Benzene, (2-bromoethoxy)-

HRID 899142Notes

Reaction equation

HRID 899142 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:8][CH2:9][CH2:10][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 68526Benzene, (2-bromoethoxy)-Yield 93.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of phenol (5 g, 0.053 mol), 1,2-dibromethane (60 g, 0.319 mol) and K2CO3 (22 g, 0.16 mol) in dry acetonitrile (100 ml) was stirred at 60° C. overnight under nitrogen atmosphere. The reaction mixture was filtered and the solvent concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 10% ethyl acetate in petroleum ether as eluent to yield (10 g) of the sub-title compound as a solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe solvent concentrated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel using 10% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-54a0425bbb74418d80d613da6246d5ea
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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