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

HRID 566598Notes

Reaction equation

HRID 566598 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
10 °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 10° 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 silica gel column chromatography (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 silica gel column chromatography (eluent: hexane/ethyl acetate=8:1)

Sources & evidence

ORD record
ord-7cb1069235704777a6244a2175d1b904
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

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