1,3-Dibromopropane → 1-(3-Bromopropoxy)-4-fluorobenzene

HRID 1588425Notes

Reaction equation

HRID 1588425 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:15][CH2:16][CH2:17][CH2:18]Br.C(COC)OC>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][CH2:17][CH2:16][Br:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 80711,2-DimethoxyethaneHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 2600041-(3-Bromopropoxy)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 11.2 g (0.1 mol) of 4-fluorophenol, 16.5 g (0.12 mol) of pulverized potassium carbonate, 20.2 g (0.1 mol) of 1,3-dibromopropane and 100 ml of anhydrous dimethoxyethane was refluxed under nitrogen for 6 hours and then cooled. The mixture was diluted with methylene chloride and washed with water. The resultant organic product solution was dried over Na2SO4 and evaporated in vacuo. The residue was chromatographed on silica gel using cyclohexane elution to give pure product.

Workup

  1. temperaturewas refluxed under nitrogen for 6 hours
  2. temperaturecooled
  3. washwashed with water
  4. dry with materialThe resultant organic product solution was dried over Na2SO4
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washcyclohexane elution
  8. customto give pure product

Sources & evidence

ORD record
ord-9931f402a44245948e7e4c9fe6d38e71
Source dataset
uspto-grants-1993_06
Patent number
US05221760

Reaction notes

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