Phosphorus tribromide → 4-(3-Bromopropoxy)1-phenoxybenzene

HRID 249359Notes

Reaction equation

HRID 249359 reaction equation
[O:1]([C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH2:14][CH2:15]O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:20]>ClC(Cl)(Cl)Cl>[O:1]([C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH2:14][CH2:15][Br:20])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 102435403-(4-Phenoxyphenoxy)-propan-1-ol

Product 1

HCID 112552434-(3-Bromopropoxy)1-phenoxybenzeneYield 192.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
40 °C

Procedure

24.4 g of 3-(4-phenoxyphenoxy)-propan-1-ol is added in portions to a solution of 9.5 g of phosphorus tribromide in 65 ml of tetrachloromethane. When the exothermic reaction has subsided, the mixture is heated for 4 hours at 40° C. After the mixture has cooled, the solvent is removed under reduced pressure, the residue is dissolved in 300 ml of methyl tert-butyl ether, and the organic phase is washed thoroughly with water and dried over sodium sulfate. The crude product remaining after removal of the solvent is purified by silica gel filtration with toluene/methyl tert-butyl ether (2:1). There is obtained 20.8 g (67%) of 3-(p-phenoxyphenoxy)-1-bromopropane; m.p.: 54°-55° C.

Workup

  1. customWhen the exothermic reaction
  2. temperatureAfter the mixture has cooled
  3. customthe solvent is removed under reduced pressure
  4. dissolutionthe residue is dissolved in 300 ml of methyl tert-butyl ether
  5. washthe organic phase is washed thoroughly with water
  6. dry with materialdried over sodium sulfate
  7. customafter removal of the solvent
  8. filtrationis purified by silica gel filtration with toluene/methyl tert-butyl ether (2:1)

Sources & evidence

ORD record
ord-4fd9c109f7734f5bacda5df11fde2ec4
Source dataset
uspto-grants-1993_05
Patent number
US05214064

Reaction notes

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