Lead (II) bromide → 3-(2,2-Dichloroethenyl)phenol

HRID 1960095Notes

Reaction equation

HRID 1960095 reaction equation
[Al].[Pb](Br)Br.[Cl:5][C:6](Cl)([Cl:16])[CH:7]([C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)O>CO>[Cl:5][C:6]([Cl:16])=[CH:7][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 24831Lead (II) bromideHCID 5359268AluminumHCID 687485713-(2,2,2-Trichloro-1-hydroxyethyl)phenol

Product 1

HCID 713284213-(2,2-Dichloroethenyl)phenolYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Aluminum (3.73 g, 0.091 mol), lead bromide (2.28 g, 0.0091 mol) and 36% HC (15.47 ml, 0.182 mol) were added to 200 ml of methanol, and 3-(2,2,2-trichloro-1-hydroxyethyl)phenol (12.57 g, 0.091 mol) obtained in Step 1 was added thereto. The mixture was stirred at 60° C. for 4 hours. The solvent was removed therefrom under a reduced pressure. Ice was added to the reaction mixture and resulting mixture was washed three times with n-hexane and ether (1:1). The organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:n-hexane=1:9) to obtain the title compound (16.0 g, 93%).

Workup

  1. additionwas added
  2. customThe solvent was removed
  3. additionIce was added to the reaction mixture
  4. customresulting mixture
  5. washwas washed three times with n-hexane and ether (1:1)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-705c28a7a40b4c05a5fc6c2be6fc71b1
Source dataset
uspto-grants-2013_04
Patent number
US08410302B2

Reaction notes

Loading…