Bromine → 4-bromo-1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile

HRID 549240Notes

Reaction equation

HRID 549240 reaction equation
C([O-])(=O)C.[K+].[Br:6]Br.[CH2:8]([N:11]1[C:15]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:14][C:13]([C:23]#[N:24])=[N:12]1)[CH2:9][CH3:10].S([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:6][C:14]1[C:13]([C:23]#[N:24])=[N:12][N:11]([CH2:8][CH2:9][CH3:10])[C:15]=1[CH2:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 24408BromineHCID 517044Potassium AcetateHCID 23665763Sodium BisulfiteHCID 671577501-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile

Product 1

HCID 671583524-bromo-1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrileYield 98.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium acetate (3.93 g, 40.0 mmol) and bromine (3.58 g, 22.4 mmol) were sequentially added to a solution of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile (3.98 g, 16 mmol) in acetic acid (32 mL). The reaction was stirred for 40 hours at room temperature. Saturated aqueous sodium hydrogensulfite was added until the reaction became colorless. Most of the acetic acid was removed under reduced pressure, and 2M aqueous sodium carbonate was added. A precipitate formed, was isolated by filtration, washed with water, and dried on the vacuum filter funnel to provide 4.91 g of 4-bromo-1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile as a white solid.

Workup

  1. customMost of the acetic acid was removed under reduced pressure, and 2M aqueous sodium carbonate
  2. additionwas added
  3. customA precipitate formed
  4. customwas isolated by filtration
  5. washwashed with water
  6. customdried on the vacuum
  7. filtrationfilter funnel

Sources & evidence

ORD record
ord-71e8c9ddfafa4b6f9a91d5c5248c46c7
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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