1,1-Dichloroethane → Chloromethyl 3-trifluoromethoxybenzoate

HRID 1880753Notes

Reaction equation

HRID 1880753 reaction equation
Cl[CH:2]([Cl:4])C.[F:5][C:6]([F:18])([F:17])[O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12].[O:19]1CCCOO1>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4].O>[F:5][C:6]([F:18])([F:17])[O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([O:19][CH2:2][Cl:4])=[O:12]

Participants

6

Reactant 3

HCID 63651,1-DichloroethaneHCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 19593658CID 19593658

Product 1

HCID 59570317Chloromethyl 3-trifluoromethoxybenzoate

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 962WaterSolvent

Procedure

To 10 ml of dichloroethane were added 0.93 g of zirconium tetrachloride and 1 g of 3-trifluoromethoxybenzoyl chloride, and the mixture was stirred at room temperature for 20 minutes. At 10° C., 0.15 g of trioxane was added, and the mixture was stirred for 30 minutes, and further stirred at room temperature for 1 hour. Water was added slowly under ice-cooling, the resultant solution was extracted with chloroform three times, and the organic layers were combined, washed with an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated to obtain 1 g of chloromethyl 3-trifluoromethoxybenzoate.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringfurther stirred at room temperature for 1 hour
  3. temperaturecooling
  4. extractionthe resultant solution was extracted with chloroform three times
  5. washwashed with an aqueous saturated sodium bicarbonate solution
  6. dry with materialan aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-57d8e3e9dbf74feaa69d6a3faf47a6cb
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…