2,4-Difluorobenzaldehyde → HCID 66613393, compound

HRID 406592Notes

Reaction equation

HRID 406592 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[C:24]1[N:28]([CH3:29])[N:27]=[C:26]([CH3:30])[CH:25]=1.FC1C=C(F)C=CC=1C=O>ClCC(Cl)(Cl)Cl>[F:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[C:8]([C:25]1[C:26]([CH3:30])=[N:27][N:28]([CH3:29])[C:24]=1[C:18]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=1[F:16])=[O:9]

Participants

6

Reactant 4

HCID 737702,4-DifluorobenzaldehydeHCID 5880812,4-Difluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59281365HCID 59281365, compound

Product 1

HCID 66613393HCID 66613393, compound

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent2×

Procedure

To a mixture of aluminum chloride (380 mg, 2.88 mmol) in tetrachloroethane (10 mL) at about 0° C. was added 2,4-difluorobenzoyl chloride (0.36 mL, 2.88 mmol). The reaction mixture was stirred for about 30 minutes, and then a mixture of 5-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole (prepared by the method analogous to Example 4, Steps A-B starting with 2,4-difluorobenzaldehyde) in tetrachloroethane (0.5 mL) was added. The reaction mixture was allowed to warm to room temperature, stirred for 1 h, and then heated at reflux for 24 h. The reaction mixture was cooled to room temperature, poured over a mixture of ice/hydrochloric acid and extracted with dichloromethane (3×). The combined organic layers were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by MPLC (50% ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (0.16 g).

Workup

  1. customprepared by the method analogous to Example 4, Steps A-B
  2. additionwas added
  3. stirringstirred for 1 h
  4. temperatureheated
  5. temperatureat reflux for 24 h
  6. temperatureThe reaction mixture was cooled to room temperature
  7. extractionextracted with dichloromethane (3×)
  8. washThe combined organic layers were washed with saturated sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting material was purified by MPLC (50% ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-d1b3ac4802e74265b42d0a1ac44cd534
Source dataset
uspto-grants-2014_06
Patent number
US08754115B2

Reaction notes

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