Potassium Carbonate → 3-(2-Chloro-4-trifluoromethoxyphenoxy)propanol

HRID 229350Notes

Reaction equation

HRID 229350 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].Br[CH2:15][CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[O:13][CH2:15][CH2:16][CH2:17][OH:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 130447832-Chloro-4-(trifluoromethoxy)phenol

Product 1

HCID 685273763-(2-Chloro-4-trifluoromethoxyphenoxy)propanolYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-4-trifluoromethoxyphenol (16.4 g, 0.077 mole) in 100 mL of acetonitrile was added 3-bromopropanol (12.87 g, 0.092 mole) and potassium carbonate (21.33 g, 0.154 mole). The resulted solution was refluxed at 75° C.-80° C. overnight. The solvent was then evaporated. The residue was dissolved in 100 mL of ethyl acetate and washed with 100 mL of H2O. The organic layer was separated, dried over MgSO4, filtered and the organic solvent was evaporated to yield 20 g of the product.

Workup

  1. temperatureThe resulted solution was refluxed at 75° C.-80° C. overnight
  2. customThe solvent was then evaporated
  3. dissolutionThe residue was dissolved in 100 mL of ethyl acetate
  4. washwashed with 100 mL of H2O
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe organic solvent was evaporated

Sources & evidence

ORD record
ord-e272d54994bb40d983421826a14aa4f3
Source dataset
uspto-grants-2009_07
Patent number
US07563792B2

Reaction notes

Loading…