Benzyl Bromide → 1-Benzyl-4-iodo-1H-pyrazole

HRID 2059599Notes

Reaction equation

HRID 2059599 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(C)=O>[CH2:13]([N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 770224-Iodopyrazole

Product 1

HCID 37945791-Benzyl-4-iodo-1H-pyrazoleYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 4-iodo-1H-pyrazole (1.50 g, 7.73 mmol) and potassium carbonate (2.67 g, 19.3 mmol) in acetone was added benzyl bromide (0.96 mL, 8.07 mmol) and the reaction was refluxed for 3 h. After cooling to room temperature the mixture was concentrated onto silica gel in vacuo and eluted through a short silica plug (sequential elution—hexane, 10% diethyl ether in hexanes) to provide the title compound as a white solid (2.12 g, 97% yield).

Workup

  1. temperaturethe reaction was refluxed for 3 h
  2. concentrationwas concentrated onto silica gel in vacuo
  3. washeluted through a short silica plug (sequential elution—hexane, 10% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-3f07b8b1c8f34afdafbc3f724656e5ef
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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