3-Bromo-1-propanol → 3-(3,5-Dibromo-4-nitropyrazol-1-yl)propan-1-ol

HRID 1181149Notes

Reaction equation

HRID 1181149 reaction equation
[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([Br:10])[NH:4][N:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][OH:17]>CN(C=O)C>[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([Br:10])[N:4]([CH2:14][CH2:15][CH2:16][OH:17])[N:3]=1

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 137079943,5-Dibromo-4-nitro-1H-pyrazole

Product 1

HCID 231041703-(3,5-Dibromo-4-nitropyrazol-1-yl)propan-1-olYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

A mixture of 3,5-dibromo-4-nitropyrazole (2) (2.0 g; 7.38 mmol) in DMF (9.5 ml) was added over 15 minutes to a suspension of NaH (0.32 g, 8.0 mmol; 60% dispersion in oil, prewashed with hexane) in DMF (16 ml) with stirring and under an inert atmosphere. After stirring for 15 minutes, a solution of 3-bromo-1-propanol (1.0 g; 7.19 mmol) in DMF (3.2 ml) was added dropwise. The reaction mixture was heated at 80° C. for 2 hours (monitored by TLC) and the DMF was then evaporated off under reduced pressure. A mixture of DCM/water (20 ml, 1/1) was added. The organic phase was dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The crude reaction product was obtained as a black oil (1.9 g, 79%), which was used without further purification in the amination step.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customthe DMF was then evaporated off under reduced pressure
  3. additionA mixture of DCM/water (20 ml, 1/1)
  4. additionwas added
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customthe solvent was evaporated off under reduced pressure
  7. customThe crude reaction product

Sources & evidence

ORD record
ord-8aa8bdc7fe944f4a808d967c3a9b2595
Source dataset
uspto-grants-2007_10
Patent number
US07285136B2

Reaction notes

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