2-Methylbenzenesulfonic acid → 4-Chloro-3-(4-chloro-2-fluoro-5-di(ethoxy)methylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

HRID 1738367Notes

Reaction equation

HRID 1738367 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.C1(C)C(S(O)(=O)=O)=CC=CC=1.[Cl:22][C:23]1[CH:30]=[C:29]([F:31])[C:28]([C:32]2[C:36]([Cl:37])=[C:35]([O:38][CH:39]([F:41])[F:40])[N:34]([CH3:42])[N:33]=2)=[CH:27][C:24]=1C=O.C(N(CC)CC)C>O1CCCC1>[Cl:37][C:36]1[C:32]([C:28]2[CH:27]=[C:24]([CH:1]([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])[C:23]([Cl:22])=[CH:30][C:29]=2[F:31])=[N:33][N:34]([CH3:42])[C:35]=1[O:38][CH:39]([F:41])[F:40]

Participants

6

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 118099222-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzaldehyde

Product 1

HCID 153898584-Chloro-3-(4-chloro-2-fluoro-5-di(ethoxy)methylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 ml of triethyl orthoformate and 0.1 g of toluenesulfonic acid were added to a solution of 3 g (8.8 mmol) of 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzaldehyde in 50 ml of tetrahydrofuran. After the mixture had been refluxed for 2 hours, it was treated with 3 ml of triethylamine. The mixture was subsequently concentrated. The residue was treated with 50 ml of water. The product was subsequently extracted from the aqueous phase using ethyl acetate. The organic phase was then washed using saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and finally concentrated. The crude product was purified by means of column chromatography on silica gel (eluent: hexane/ethyl acetate=9:1). Yield: 1 g.

Workup

  1. temperatureAfter the mixture had been refluxed for 2 hours
  2. concentrationThe mixture was subsequently concentrated
  3. additionThe residue was treated with 50 ml of water
  4. extractionThe product was subsequently extracted from the aqueous phase
  5. washThe organic phase was then washed
  6. dry with materialdried over magnesium sulfate
  7. concentrationfinally concentrated
  8. customThe crude product was purified by means of column chromatography on silica gel (eluent: hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-6a7fc2db7ada487c90bb3e507e8e4210
Source dataset
uspto-grants-1999_10
Patent number
US05962694

Reaction notes

Loading…