Triethylamine → 3-(2-Chloro-4-trifluoromethoxyphenoxy)propyl methane sulfonate

HRID 229351Notes

Reaction equation

HRID 229351 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][OH:8].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>ClCCl>[CH3:18][S:19]([O:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1[CH:9]=[CH:10][C:11]([O:13][C:14]([F:16])([F:15])[F:17])=[CH:12][C:2]=1[Cl:1])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 685273763-(2-Chloro-4-trifluoromethoxyphenoxy)propanol

Product 1

HCID 865928333-(2-Chloro-4-trifluoromethoxyphenoxy)propyl methane sulfonateYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-chloro-4-trifluoromethoxyphenoxy)-propanol (20 g, 0.074 mole) in 100 mL of dichloromethane at 0° C. was added methanesulfonyl chloride (6.83 mL, 0.089 mole) and triethylamine (20.5 mL, 0.148 mole). The resulting solution was stored in a refrigerator overnight. The solution was then washed with 100 mL of cooled, diluted HCl-H2O solution. The organic layer was separated, dried over MgSO4, filtered and evaporated of solvent to yield 25.4 g of the product.

Workup

  1. customwas stored in a refrigerator overnight
  2. washThe solution was then washed with 100 mL
  3. temperatureof cooled
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated of solvent

Sources & evidence

ORD record
ord-4770e3ef45524b14bf0d3d98a853c310
Source dataset
uspto-grants-2009_07
Patent number
US07563792B2

Reaction notes

Loading…