Pyridine → 1-(3-Bromo-4-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butene-1-one

HRID 2386155Notes

Reaction equation

HRID 2386155 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:25])[CH2:10][C:11]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)(O)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[CH3:8].S(Cl)(Cl)=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:25])[CH:10]=[C:11]([C:17]2[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=2)[C:12]([F:14])([F:15])[F:13])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 866480671-(3-Bromo-4-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutane-1-one

Product 1

HCID 866480681-(3-Bromo-4-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butene-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 6.00 g of 1-(3-bromo-4-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutane-1-one and 4.70 g of thionyl chloride in 30 mL of toluene, 3.12 g of pyridine was added while heating and stirring the solution at 80° C. and the resultant reaction mixture was continued to be stirred at the same temperature further for 2 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and was diluted with 30 mL of toluene, and the diluted reaction mixture was washed with water (30 mL×1). Subsequently, the washed reaction mixture was dehydrated and dried over a saturated brine and anhydrous magnesium sulfate in this order and the solvent was distilled off under reduced pressure to obtain 6.04 g of the objective substance as a yellow oily substance.

Workup

  1. temperaturewhile heating
  2. customthe resultant reaction mixture
  3. stirringto be stirred at the same temperature further for 2 hours
  4. customAfter the completion of the reaction
  5. waitthe reaction mixture was left
  6. temperatureto be cooled down to room temperature
  7. customthe diluted reaction mixture
  8. washwas washed with water (30 mL×1)
  9. customSubsequently, the washed reaction mixture
  10. dry with materialdried over a saturated brine and anhydrous magnesium sulfate in this order
  11. distillationthe solvent was distilled off under reduced pressure
  12. customto obtain 6.04 g of the objective substance as a yellow oily substance

Sources & evidence

ORD record
ord-e54c5eedb46e4067803b78343bb092eb
Source dataset
uspto-grants-2012_09
Patent number
US08268754B2

Reaction notes

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