4-Bromophenol → 1-bromo-4-propoxybenzene

HRID 361432Notes

Reaction equation

HRID 361432 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[CH2:16][CH3:17]>CC(C)=O.[I-].[K+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 27341981-bromo-4-propoxybenzeneYield 87.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 4-bromophenol (8.65 g), potassium iodide (83 mg), potassium carbonate (6.9 g) and propyl bromide (6.15 g) was heated under reflux in acetone (100 ml) for 48 hours. The reaction was cooled to ambient temperature, filtered and the acetone removed in vacuo to give an amber oil. This was purified by gradient elution with 20% ethyl acetate/isohexane through a silica gel Mega Bond Elut column to give 1-bromo-4-propoxybenzene (9.4 g) as a clear oil, mass spectrum (+ve CI): 214 (M+H)+.

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. customthe acetone removed in vacuo
  4. customto give an amber oil
  5. customThis was purified by gradient elution with 20% ethyl acetate/isohexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-67b307fb73e0408e9bb8eb82b83f3157
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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