Sodium Carbonate → 4-Bromo-1-(1,1-dimethylethyl)-1H-pyrazole

HRID 57846Notes

Reaction equation

HRID 57846 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]([N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1)([CH3:10])([CH3:9])[CH3:8].[Br:16]Br>C(Cl)Cl>[Br:16][C:14]1[CH:13]=[N:12][N:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 134698151-tert-Butyl-1H-pyrazole

Product 1

HCID 532168984-Bromo-1-(1,1-dimethylethyl)-1H-pyrazoleYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Na2CO3 (3.6 g, 33.9 mmol) in CH2Cl2 (30 mL) was added 1-tert-butyl-1H-pyrazole (2.1 g, 17 mmol) and Br2 (0.9 mL). The mixture was stirred at room temperature overnight. The formed solid was removed by filtration and the filter cake was washed with CH2Cl2 (30 mL). The filtrates were washed with water (20 mL) and brine (20 mL), dried (MgSO4), and concentrated under reduced pressure to afford crude 4-bromo-1-tert-butyl-1H-pyrazole (2.9 g, 85%), which was used in next step without further purification. MS (ESI) m/z: 203 [M+H]+.

Workup

  1. customThe formed solid was removed by filtration
  2. washthe filter cake was washed with CH2Cl2 (30 mL)
  3. washThe filtrates were washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7ee0fd5430a4c08954959ed1e84585a
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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