Sulfuric Acid → 2-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzaldehyde

HRID 1738365Notes

Reaction equation

HRID 1738365 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([CH:18](Br)Br)[C:15]([Cl:21])=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].S(=O)(=O)(O)[OH:24]>>[Cl:21][C:15]1[CH:14]=[C:13]([F:22])[C:12]([C:3]2[C:2]([Cl:1])=[C:6]([O:7][CH:8]([F:10])[F:9])[N:5]([CH3:11])[N:4]=2)=[CH:17][C:16]=1[CH:18]=[O:24]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 150305704-chloro-3-(4-chloro-5-dibromomethyl-2-fluorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

Product 1

HCID 118099222-Chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorobenzaldehyde

Conditions

Temperature
100 °C

Procedure

68 g (0.14 mol) of 4-chloro-3-(4-chloro-5-dibromomethyl-2-fluorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole were dissolved in 200 ml of concentrated sulfuric acid, with ice-cooling, whereupon the mixture was heated at 100° C. until the evolution of gas had ceased. It was then poured into 4 l of ice-water. The mixture was subsequently extracted three times using ethyl acetate. The combined organic phases were washed with water, then dried over magnesium sulfate and finally concentrated. The crude product was purified by means of column chromatography on silica gel (eluent: hexane/ethyl acetate=8:1). Yield: 35 g; m.p.: 95-98° C.

Workup

  1. temperaturecooling, whereupon the mixture
  2. extractionThe mixture was subsequently extracted three times
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationfinally concentrated
  6. customThe crude product was purified by means of column chromatography on silica gel (eluent: hexane/ethyl acetate=8:1)

Sources & evidence

ORD record
ord-4aa1be6deb7a4966baf97cdd4aee8f4f
Source dataset
uspto-grants-1999_10
Patent number
US05962694

Reaction notes

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