4-Bromophenol → 1-Bromo-4-(4-bromobutoxy)benzene

HRID 1816769Notes

Reaction equation

HRID 1816769 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11][CH2:12][CH2:13]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:12][CH2:11][CH2:10][Br:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 80561,4-DibromobutaneHCID 11430Potassium Carbonate

Product 1

HCID 80633591-Bromo-4-(4-bromobutoxy)benzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromophenol (3 g) and 1,4-dibromobutane (6.2 ml) in N,N-dimethylformamide (30 ml) was treated with potassium carbonate (2.89 g) at room temperature for 27 hours. The mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, filtered, and evaporated. The residue was purified by silica gel chromatography (25:1 hexane-ethyl acetate elution) to give 1-bromo-4-(4-bromobutoxy)benzene (3.09 g).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography (25:1 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-f9fe90f1826b433a9035dd98e41faffc
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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