3,4-Dichlorophenol → 4-(3-Bromopropoxy)-1,2-dichlorobenzene

HRID 2371613Notes

Reaction equation

HRID 2371613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:10][CH2:11][CH2:12][CH2:13]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][CH2:13][CH2:12][CH2:11][Br:10]

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 80011,3-DibromopropaneHCID 14798Sodium Hydroxide

Product 1

HCID 117810424-(3-Bromopropoxy)-1,2-dichlorobenzene

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.26 g (20 mmol) of 3,4-dichlorophenol, 20.2 g (100 mmol) of 1,3-dibromopropane, 6.80 g (20 mmol) of tetra-n-butyl ammonium hydrogen sulfate, 40 ml of 1N sodium hydroxide, and 40 ml of methylene chloride was stirred rapidly at reflux. After 2 hours, the mixture was allowed to cool and the layers were separated. The organic layer was washed with water, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was chromatographed over silica gel using methylene chloride/hexane as eluent. The title compound (1.58 g) was found to be homogeneous by thin layer chromatography (10% by volume of methylene chloride/hexane on silica gel plates).

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. customthe layers were separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-08d7d1d4443a4f4085405ad948da23b4
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

Loading…