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

HRID 2249042Notes

Reaction equation

HRID 2249042 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-29c8760439c546efbf2dadaf4445cfbd
Source dataset
uspto-grants-1991_08
Patent number
US05041638

Reaction notes

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