Potassium Hydroxide → 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazole

HRID 895685Notes

Reaction equation

HRID 895685 reaction equation
Br[CH:2]([C:5]1[C:6]([C:12]([F:15])([F:14])[F:13])=[N:7][N:8]([CH3:11])[C:9]=1[CH3:10])[CH2:3]Br.[OH-].[K+]>C1(C)C=CC=CC=1>[C:2]([C:5]1[C:6]([C:12]([F:14])([F:15])[F:13])=[N:7][N:8]([CH3:11])[C:9]=1[CH3:10])#[CH:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 223809914-(1,2-Dibromoethyl)-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazole

Product 1

HCID 104424634-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazoleYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.3 g (20.9 mmol) of 4-(1,2-dibromoethyl)-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole are taken up in 5 ml of toluene and heated to 70° C. for 12 h together with a 60% aqueous KOH solution (10 ml) and 1.2 g of polyethylene glycol 600. After the end of the reaction, the two phases are separated, the aqueous phase is extracted with toluene and the combined organic phases are dried over MgSO4 and concentrated. The product is obtained as a solid in an 81% yield.

Workup

  1. customAfter the end of the reaction
  2. customthe two phases are separated
  3. extractionthe aqueous phase is extracted with toluene
  4. dry with materialthe combined organic phases are dried over MgSO4
  5. concentrationconcentrated
  6. customThe product is obtained as a solid in an 81% yield

Sources & evidence

ORD record
ord-2deab906e34649328e8697086aeb03d8
Source dataset
uspto-grants-2005_07
Patent number
US06916839B2

Reaction notes

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