Carbon Tetrachloride → Ethyl 4-(bromomethyl)-3-phenylisoxazole-5-carboxylate

HRID 2388167Notes

Reaction equation

HRID 2388167 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH: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>C(Cl)Cl>[Br:25][CH2:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][O:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 58374134HCID 58374134, compound

Product 1

HCID 67530071Ethyl 4-(bromomethyl)-3-phenylisoxazole-5-carboxylateYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-methyl-3-phenylisoxazole-5-carboxylate (0.2 g, 0.87 mmol), NBS (0.17 g, 0.95 mmol), and benzoyl peroxide (21 mg, 0.087 mmol) were added to 5 mL of carbon tetrachloride and the mixture was refluxed for 16 h. The mixture was diluted with CH2Cl2, and 5 g of silica gel was added. The solvent was removed in vacuo and the crude was purified by flash chromatography (0-20% EtOAc/hexanes) to give 214 mg of the title compound. MS: (+) m/z 310.31, 312.28 (M+1, 79Br/81Br).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. additionwas added
  3. customThe solvent was removed in vacuo
  4. customthe crude was purified by flash chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6fbac8dd97144bf2a02c566ceed18fac
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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