Benzoyl Peroxide → tert-butyl 4-(bromomethyl)-1H-pyrazole-1-carboxylate

HRID 390407Notes

Reaction equation

HRID 390407 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH3:13])[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:14]N1C(=O)CCC1=O.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[CH:12]=[C:11]([CH2:13][Br:14])[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 23021524HCID 23021524, compound

Product 1

HCID 58066672tert-butyl 4-(bromomethyl)-1H-pyrazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.875 g, 4.8 mmol), N-bromosuccinimide (0.897 g, 5.0 mmol), and benzoyl peroxide (0.058 g, 0.24 mmol) were combined in CCl4 (50 mL). The reaction was heated to reflux and stirred under a halogen lamp for 1 hour. The mixture was filtered and concentrated, and the residue was purified by silica gel chromatography to give the title compound, contaminated with a small amount of starting material.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-78aadb8ee46245679e2024f560247d5d
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

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