Ethylene Glycol → 4-chloro-3-(4-chloro-5-(1,3-dioxolan-2-yl)-2-fluorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

HRID 1198433Notes

Reaction equation

HRID 1198433 reaction equation
O.[Cl:2][C:3]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:16]([Cl:17])=[C:15]([C:18]([F:21])([F:20])[F:19])[N:14]([CH3:22])[N:13]=2)=[CH:7][C:4]=1[CH:5]=[O:6].[CH2:23](O)[CH2:24][OH:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:17][C:16]1[C:12]([C:8]2[CH:7]=[C:4]([CH:5]3[O:25][CH2:24][CH2:23][O:6]3)[C:3]([Cl:2])=[CH:10][C:9]=2[F:11])=[N:13][N:14]([CH3:22])[C:15]=1[C:18]([F:21])([F:20])[F:19]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 120071322-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzaldehyde

Product 1

HCID 194367504-chloro-3-(4-chloro-5-(1,3-dioxolan-2-yl)-2-fluorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazoleYield 61.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In an apparatus equipped with a Dean-Stark trap for azeotropic removal of water, 2.4 g (7.0 mmoles) 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzaldehyde, 0.4 mL (7.7 mmoles) ethylene glycol and a catalytic amount of p-toluene-sulfonic acid in 50 mL toluene was heated to reflux for 24 hours. The resultant mixture was concentrated and the residue purified by chromatography to give 1.65 g (61%) of 4-chloro-3-(4-chloro-5-(1,3-dioxolan-2-yl)-2-fluorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole as a clear colorless oil; nD25 1.5348.

Workup

  1. temperatureto reflux for 24 hours
  2. concentrationThe resultant mixture was concentrated
  3. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-0a95d79cf6634cba859bdae6d51ab205
Source dataset
uspto-grants-1994_01
Patent number
US05281571

Reaction notes

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