3-Bromo-1,2-propanediol → HCID 13007227, compound

HRID 1181152Notes

Reaction equation

HRID 1181152 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][CH:15]([OH:18])[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][CH:15]([OH:18])[CH2:16][OH:17])[N:3]=1

Participants

5

Reactant 3

HCID 208273-Bromo-1,2-propanediolHCID 24758Sodium hydrideHCID 137079943,5-Dibromo-4-nitro-1H-pyrazole

Product 1

HCID 13007227HCID 13007227, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

A mixture of 3,5-dibromo-4-nitropyrazole (2) (40.0 g; 147 mmol) in DMF (200 ml) was added over 15 minutes to a suspension of NaH (6.5 g, 162 mmol; 60% dispersion in oil, prewashed with hexane) in DMF (320 ml) with stirring and under an inert atmosphere. After stirring for 30 minutes, a solution of 3-bromo-1,2-propanediol (19.4 ml; 221 mmol) in DMF (80 ml) was added dropwise. The reaction mixture was heated at 80° C. for 3 hours and the DMF was then evaporated off under reduced pressure. A mixture of DCM/water (480 ml, 2/1) was added. A yellow solid precipitated out. After washing with ether (50 ml), the 3-(3,5-dibromo-4-nitropyrazol-1-yl)-propane-1,2-diol (32.3 g, 63%) was obtained as a white solid (23.3 g; 48%).

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe DMF was then evaporated off under reduced pressure
  3. additionA mixture of DCM/water (480 ml, 2/1)
  4. additionwas added
  5. customA yellow solid precipitated out
  6. washAfter washing with ether (50 ml)

Sources & evidence

ORD record
ord-bf8901d354dd4425a4acf49e33288085
Source dataset
uspto-grants-2007_10
Patent number
US07285136B2

Reaction notes

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