Iodoethane → 4-Bromo-1-ethyl-3-(4-nitrophenyl)-1H-pyrazole

HRID 28916Notes

Reaction equation

HRID 28916 reaction equation
[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)=[N:4][NH:5][CH:6]=1.[H-].[Na+].I[CH2:19][CH3:20]>CN(C)C=O>[Br:1][C:2]1[C:3]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)=[N:4][N:5]([CH2:19][CH3:20])[CH:6]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178526566HCID 178526566, compound

Product 1

HCID 689971424-Bromo-1-ethyl-3-(4-nitrophenyl)-1H-pyrazoleYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. solution of 4-bromo-3-(4-nitrophenyl)-1H-pyrazole (485 mmol) in N,N-dimethylformamide (1000 mL) was slowly treated with sodium hydride (485 mmol) and then iodoethane (582 mmol). The reaction mixture was stirred for 30 minutes at room temperature and then poured into ice-water (1000 mL). Product precipitated out of solution and was collected by filtration, washed with water (4×500 mL) and dried to provide the title product as a light brown powder (94%). ESMS [M+H]+: 297.2

Workup

  1. customProduct precipitated out of solution
  2. filtrationwas collected by filtration
  3. washwashed with water (4×500 mL)
  4. customdried

Sources & evidence

ORD record
ord-d4272db90373478088b87e3dde140d48
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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