Water → HCID 86761698, compound

HRID 1880246Notes

Reaction equation

HRID 1880246 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12](O)([C:24]([F:27])([F:26])[F:25])[CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([Cl:23])[CH:17]=2)=[O:15])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(Cl)(Cl)=O.N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([C:24]([F:27])([F:25])[F:26])=[CH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([Cl:23])[CH:17]=2)=[O:15])[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86761699HCID 86761699, compound

Product 1

HCID 86761698HCID 86761698, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4.28 g of 3-[3-bromo-5-(trifluoromethyl)phenyl]-1-(3-chloro-4-methylphenyl)-4,4,4-trifluoro-3-hydroxybutane-1-one in 10 mL of toluene, 2.08 g of thionyl chloride and 1.38 g of pyridine were added while stirring the solution at 80° C. to continue the stirring of the resultant mixture at the same temperature for 2 hours. After the completion of the reaction, 10 mL of water was added to the reaction mixture while ice-cooling the reaction mixture and the stirring of the reaction mixture was continued until the temperature of the reaction mixture returned to room temperature. The organic phase was separated off and charged into a solution of 0.77 g of sodium hydroxide in 5 mL of water. The resultant mixture was stirred at room temperature for 30 minutes. The organic phase was separated off and then was dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order. The solvent was distilled off under reduced pressure to obtain 4.02 g of a crude objective substance as a yellow oily substance. This substance was used in the next process as it was without being further purified.

Workup

  1. additionwas added to the reaction mixture while ice-
  2. temperaturecooling the reaction mixture
  3. stirringthe stirring of the reaction mixture
  4. customreturned to room temperature
  5. customThe organic phase was separated off
  6. additioncharged into a solution of 0.77 g of sodium hydroxide in 5 mL of water
  7. stirringThe resultant mixture was stirred at room temperature for 30 minutes
  8. customThe organic phase was separated off
  9. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  10. distillationThe solvent was distilled off under reduced pressure
  11. customto obtain 4.02 g of a crude objective substance as a yellow oily substance

Sources & evidence

ORD record
ord-a8fe20077a95429288a0b4ef3d887709
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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