Bromine → HCID 66959135, compound

HRID 1984496Notes

Reaction equation

HRID 1984496 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])=[CH:8][C:7]([C:15]#[N:16])=[N:6]1)[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[K+].[Br:22]Br>>[CH2:1]([N:5]1[C:9]([CH2:10][C:11]([OH:14])([CH3:12])[CH3:13])=[C:8]([Br:22])[C:7]([C:15]#[N:16])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 66959096HCID 66959096, compound

Product 1

HCID 66959135HCID 66959135, compoundYield 53.5%

Conditions

Temperature
0 °C

Procedure

The method described in Part F of Examples 1 through 4 was used to treat 1-butyl-5-(2-hydroxy-2-methylpropyl)-1H-pyrazole-3-carbonitrile (18 g, 81 mmol) with potassium acetate (16.7 g, 171 mmol) and bromine (4.6 mL, 89 mmol). After the acetic acid was removed under reduced pressure, the residue was diluted with dichloromethane (100 mL) and adjusted to pH 12 with the addition of 50% w/w aqueous sodium hydroxide and ice while maintaining the temperature at 0° C. The resulting mixture was extracted with dichloromethane, and the combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (60I cartridge, eluting with 0 to 50% ethyl acetate in hexanes to provide 13 g of 1-butyl4-bromo-5-(2-hydroxy-2-methylpropyl)-1H-pyrazole-3-carbonitrile as a yellow oil.

Workup

  1. customAfter the acetic acid was removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane (100 mL)
  3. additionadjusted to pH 12 with the addition of 50% w/w aqueous sodium hydroxide and ice
  4. extractionThe resulting mixture was extracted with dichloromethane
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by chromatography on a HORIZON HPFC system (60I cartridge
  9. washeluting with 0 to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f66c5d14532440cc8b3ad386b0aa6949
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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