Benzoyl Peroxide → Ethyl 4-(bromomethyl)-3-(pyridin-4-yl)isoxazole-5-carboxylate

HRID 2388196Notes

Reaction equation

HRID 2388196 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:4][O:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C1C(=O)N([Br:25])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:1][C:2]1[C:3]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[N:4][O:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67530753Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate

Product 1

HCID 67531296Ethyl 4-(bromomethyl)-3-(pyridin-4-yl)isoxazole-5-carboxylateYield 21.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate (5.1 g, 22.0 mmol), NBS (4.7 g, 26.4 mmol), and benzoyl peroxide (0.53 g, 2.2 mmol) were added to 140 mL of carbon tetrachloride and the mixture was refluxed for 16 h. Solvent was removed in vacuo and the crude product was purified by flash chromatography (10-60% EtOAc/hexanes) to afford 1.5 g of the title compound. MS: (+) m/z 311, 313 (M+1, 79Br/81Br).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. customSolvent was removed in vacuo
  3. customthe crude product was purified by flash chromatography (10-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e486d625b49a4cd38648b78983898121
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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