Bromine → HCID 66959124, compound

HRID 1984413Notes

Reaction equation

HRID 1984413 reaction equation
[Br:1]Br.C([O-])(=O)C.[K+].[CH2:8]([N:12]1[C:16]([CH2:17][CH2:18][S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])=[CH:15][C:14]([C:25]#[N:26])=[N:13]1)[CH2:9][CH2:10][CH3:11].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:1][C:15]1[C:14]([C:25]#[N:26])=[N:13][N:12]([CH2:8][CH2:9][CH2:10][CH3:11])[C:16]=1[CH2:17][CH2:18][S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 66958443HCID 66958443, compound

Product 1

HCID 66959124HCID 66959124, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.8 mL, 14.7 mmol) was added dropwise to a stirred solution of potassium acetate (2.00 g, 20.1 mmol) and 1-butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carbonitrile ( 3.80 g, 13.4 mmol) in acetic acid (27 mL). The reaction was stirred at ambient temperature, then was concentrated under reduced pressure to afford a solid. Saturated aqueous sodium bicarbonate was added to the solid until the mixture was pH 9. The mixture was extracted with dichloromethane (2×50 mL). The organic layers were combined and concentrated under reduced pressure to afford a brown oil. The crude product was purified by flash chromatography (silica gel, elution with 40% ethyl acetate in hexanes) to yield 2.85 g of 4-bromo-1-butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carbonitrile as a white solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto afford a solid
  3. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  4. concentrationconcentrated under reduced pressure
  5. customto afford a brown oil
  6. customThe crude product was purified by flash chromatography (silica gel, elution with 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2d97a891312a4fe2b3b90c73ae0541b8
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

Loading…