Benzoyl Peroxide → HCID 21845938, compound

HRID 1188732Notes

Reaction equation

HRID 1188732 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:13])=[CH:11][CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]([CH2:13][Br:21])=[CH:11][CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21845879HCID 21845879, compound

Product 1

HCID 21845938HCID 21845938, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-methyl-pyrazole-1-carboxylic acid tert-butyl ester in CCl4 (40 mL) was added NBS (3.3 g, 18.5 mmol) and benzoylperoxide (450 mg, 1.86 mmol). The reaction mixture was heated to reflux for 4 h and cooled to rt. The insoluble material was filtered off and the solution was diluted with EtOAc. The organics were washed with saturated NaHCO3 and H2O, dried with Na2SO4, and concentrated. The crude product was purified by combi-flash to give 1.67 g of 5-bromomethyl-pyrazole-1-carboxylic acid tert-butyl ester in 52% yield.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationThe insoluble material was filtered off
  4. additionthe solution was diluted with EtOAc
  5. washThe organics were washed with saturated NaHCO3 and H2O
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified by combi-flash

Sources & evidence

ORD record
ord-e186a14953d74268af24e1fee09d51e0
Source dataset
uspto-grants-2014_03
Patent number
US08674088B2

Reaction notes

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