Bromine → HCID 66958984, compound

HRID 2283782Notes

Reaction equation

HRID 2283782 reaction equation
[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[N:6]=[C:5]([C:11]#[N:12])[CH:4]=1)[CH3:2].C([O-])(=O)C.[K+].[Br:18]Br.S([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:18][C:4]1[C:5]([C:11]#[N:12])=[N:6][N:7]([CH2:8][CH2:9][CH3:10])[C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 24408Bromine4×HCID 517044Potassium AcetateHCID 23665763Sodium BisulfiteHCID 66959005HCID 66959005, compound

Product 1

HCID 66958984HCID 66958984, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Ethyl-1-propyl-1H-pyrazole-3-carbonitrile (4.89 g, 30.0 mmol) was dissolved in glacial acetic acid (30 mL) and treated with potassium acetate (4.41 g, 44.9 mmol) and bromine (4.79 g, 30.0 mmol). During the slow addition of bromine, an exotherm occurred and ice bath was used to cool the reaction. After the addition of bromine was complete, the reaction was allowed to warm to ambient temperature and stir for 5 hours. Saturated aqueous sodium hydrogensulfite was added to reduce the residual bromine. The mixture was concentrated under reduced pressure and 2 M aqueous sodium carbonate was added to adjust the mixture to pH 9. The mixture was extracted with chloroform (3×100 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated to yield 6.12 g of 4-bromo-5-ethyl-1-propyl-1H-pyrazole-3-carbonitrile as a yellow oil.

Workup

  1. customice bath was used
  2. temperatureto cool
  3. customthe reaction
  4. concentrationThe mixture was concentrated under reduced pressure and 2 M aqueous sodium carbonate
  5. additionwas added
  6. extractionThe mixture was extracted with chloroform (3×100 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-df46ae8f91b64ae0829117b4a2126763
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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