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

HRID 549245Notes

Reaction equation

HRID 549245 reaction equation
C([O-])(=O)C.[K+].[Br:6]Br.[CH3:8][O:9][CH2:10][CH2:11][N:12]1[C:16]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:15][C:14]([C:24]#[N:25])=[N:13]1.S([O-])(O)=O.[Na+]>C(O)(=O)C.O>[Br:6][C:15]1[C:14]([C:24]#[N:25])=[N:13][N:12]([CH2:11][CH2:10][O:9][CH3:8])[C:16]=1[CH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 24408BromineHCID 517044Potassium AcetateHCID 23665763Sodium BisulfiteHCID 671574891-(2-Methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile

Product 1

HCID 671576704-bromo-1-(2-methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrileYield 90.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Potassium acetate (3.12 g, 31.7 mmol) and bromine (2.84 g, 17.7 mmol) were sequentially added to a solution of 1-(2-methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile (3.16 g, 12.7 mmol) in acetic acid (25 mL). The reaction was stirred for 16 hours at room temperature. Saturated aqueous sodium hydrogensulfite was added until the reaction became colorless. Water was added, and a precipitate formed, was isolated by filtration, washed with water, and dried on the vacuum filter funnel to provide 3.78 g of 4-bromo-1-(2-methoxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carbonitrile as a white solid containing about 2 mol % acetic acid.

Workup

  1. customa precipitate formed
  2. customwas isolated by filtration
  3. washwashed with water
  4. customdried on the vacuum
  5. filtrationfilter funnel

Sources & evidence

ORD record
ord-b31a214119004e15a1b30be08ad3338e
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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