Butyl bromide → HCID 18929402, compound

HRID 1598522Notes

Reaction equation

HRID 1598522 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:17]=[C:16]([S:18][CH3:19])[NH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH2:27][CH2:28][CH3:29]>CC(C)=O>[CH2:26]([N:15]1[C:16]([S:18][CH3:19])=[CH:17][C:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4]=2[Cl:12])=[N:14]1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 178503086HCID 178503086, compound2×

Product 1

HCID 18929402HCID 18929402, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 0.8 g of 3-(2,6-dichloro-4-trifluoromethylphenyl)-5-(methylsulfenyl)pyrazole (compound 16), 0.7 g of anhydrous potassium carbonate and 0.4 g of n-butyl bromide in 25 ml of acetone were refluxed for 4 hours. The reaction mixture was filtered through Celite, the filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel (eluent: ether/hexane=1/20) to obtain 0.3 g of the desired product in the form of a light brown oil (yield 69.6%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by column chromatography on silica gel (eluent: ether/hexane=1/20)

Sources & evidence

ORD record
ord-23a13f6cf5f74087b7efa0e3ec169be8
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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