Sodium Iodide → 3-bromo-4-(iodomethyl)-1-tert-pentyl-1H-pyrazole

HRID 880915Notes

Reaction equation

HRID 880915 reaction equation
[Br:1][C:2]1[C:6]([CH2:7]Cl)=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1.[I-:14].[Na+]>CC(C)=O>[Br:1][C:2]1[C:6]([CH2:7][I:14])=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 674915603-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole

Product 1

HCID 674914913-bromo-4-(iodomethyl)-1-tert-pentyl-1H-pyrazoleYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole (725 mg, 2.73 mmol) in acetone (25 mL) was added sodium iodide (4.09 g, 27.3 mmol). The reaction was heated at reflux for 2 hours, then cooled to room temperature and stirred overnight. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium thiosulfate and brine. The organics were dried over sodium sulfate, filtered, and concentrated to yield the title compound (824 mg, 85%) as a brown oil. 1H NMR (400 MHz, CDCl3, δ): 7.47 (s, 1H), 4.26 (s, 2H), 1.83 (q, J=7.41 Hz, 2H), 1.50 (s, 6H), 0.67 (t, J=7.51 Hz, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated aqueous sodium thiosulfate and brine
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5a4b9e6ace1d44b3938a04aa5bfb1480
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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