Benzyl Bromide → 1-Benzyl-1H-pyrazole
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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. IH NMR 5.29 (s, 2H), 7.18-7.28 (m, 2H), 7.28-7.40 (m, 4H), 7.53 (s, 1H).
Workup
- customReaction mixture
- concentrationwas concentrated in vacuo
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-492c50c29e404c1ca0b09917d84bc638
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855818B2
Reaction notes
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