2,4,6-Trichlorophenol → 2-(2-Bromoethoxy)-1,3,5-trichlorobenzene

HRID 2352548Notes

Reaction equation

HRID 2352548 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:5]=1[OH:12].[Br:13][CH2:14][CH2:15]Br>O.C(O)C>[Br:13][CH2:14][CH2:15][O:12][C:5]1[C:4]([Cl:3])=[CH:9][C:8]([Cl:10])=[CH:7][C:6]=1[Cl:11]

Participants

6

Reactant 3

HCID 69142,4,6-TrichlorophenolHCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide

Product 1

HCID 135651032-(2-Bromoethoxy)-1,3,5-trichlorobenzeneYield 67.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (7.8 g, 0.195 mol) in water (20 ml) was added to a solution of 2,4,6-trichlorophenol (38.0 g, 0.192 mol) in ethanol (200 ml). 1,2-dibromoethane (47 g, 0.25 mol) was then added and the resultant mixture was refluxed overnight. On cooling, the solid was filtered off and the filtrate concentrated under reduced pressure. Ether was added to the residue and the solution was then washed with dilute sodium hydroxide solution and dried over anhydrous magnesium sulphate. After removal of the solvent by evaporation, the residue was recrystallised from ethanol to give 1-bromo-2-(2,4,6-trichlorophenoxy)ethane as a white solid (39.4 g). A mixture of the 1-bromo-2-(2,4,6-trichlorophenoxy) ethane (20.0 g, 0.066 mol), triethylamine (6.7 g, 0.066 mol) and propylamine (3.9 g, 0.066 mol) in ethanol (500 ml) was then refluxed overnight. After removal of the solvent by evaporation, the residue was dissolved in ether, washed with water and dried (MgSO4). Evaporation of the solvent left an oil which, after flash chromatography on silica gel using chloroform as the eluant, yielded N-propyl-N-2-(2,4,6-trichlorophenoxy)ethylamine as an oil (12.6 g).

Workup

  1. temperatureOn cooling
  2. filtrationthe solid was filtered off
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionEther was added to the residue
  5. washthe solution was then washed with dilute sodium hydroxide solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customAfter removal of the solvent
  8. customby evaporation
  9. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-9a22dda3112f4992adde414dd8e0e307
Source dataset
uspto-grants-1989_10
Patent number
US04877802

Reaction notes

Loading…