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

HRID 1848313Notes

Reaction equation

HRID 1848313 reaction equation
S(Cl)(Cl)=O.N1C=CC=CC=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:34])[CH2:19][C:20]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)(O)[C:21]([F:24])([F:23])[F:22])=[CH:14][C:13]=1[CH3:35]>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:34])[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=2)[C:21]([F:23])([F:24])[F:22])=[CH:14][C:13]=1[CH3:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 866264261-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one

Product 1

HCID 765635821-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-oneYield 84.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

0.391 g of thionyl chloride and 0.104 g of pyridine were added to toluene (3 g) solution of 0.3 g of 1-(4-bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-3-hydroxy-4,4,4-trifluorobutan-1-one synthesized in Step 3 at room temperature and stirred for 1 hour at 80° C. After completion of the reaction, the reaction solution was cooled to room temperature, and separated by adding toluene and 2N hydrochloric acid. The organic phase was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Although the obtained residue includes a mixture of geometric isomers, this residue was purified by silica gel column chromatography which eluted the residue with ethyl acetate-hexane (1:10) to obtain 0.244 g of the target product as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled to room temperature
  3. customseparated
  4. additionby adding toluene and 2N hydrochloric acid
  5. washThe organic phase was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. additiona mixture of geometric isomers
  9. customthis residue was purified by silica gel column chromatography which
  10. washeluted the residue with ethyl acetate-hexane (1:10)

Sources & evidence

ORD record
ord-2128fb8fe784435d80df0afa7c92bea3
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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