Benzyl Bromide → 1-Benzyl-1H-pyrazole

HRID 1835068Notes

Reaction equation

HRID 1835068 reaction equation
I[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[CH2:9]([N:4]1[CH:3]=[CH:2][CH:6]=[N:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 770224-Iodopyrazole

Product 1

HCID 35464411-Benzyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodopyrazole (400 mg, 2 mmol) in DMF(4 mL) at 0 C. was added sodiumhydride (80 mg, 60% dispersion in mineral oil, 2 mmol) followed by benzyl bromide (342 mg, 2 mmol) and reaction micture was allowed to stir for 2 h. Reaction mixture was concentrated in vacuo and the residue was purified by column chromatography to give N-benzylpyrazole in almost quantitative yield. 1H NMR 5.29 (s, 2H), 7.18-7.28 (m,2H), 7.28-7.40 (m, 4H), 7.53 (s, 1H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6b7fbf7a04034a91b086b61f1d0f6c9a
Source dataset
uspto-grants-2004_08
Patent number
US06770634B1

Reaction notes

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