Benzoyl Peroxide → Ethyl 4-(bromomethyl)-3-(thiophen-2-yl)isoxazole-5-carboxylate

HRID 2388189Notes

Reaction equation

HRID 2388189 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:4][O:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C1C(=O)N([Br:24])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:1][C:2]1[C:3]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=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 67530636Ethyl 4-methyl-3-(thiophen-2-yl)isoxazole-5-carboxylate

Product 1

HCID 67530400Ethyl 4-(bromomethyl)-3-(thiophen-2-yl)isoxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 4-methyl-3-(thiophen-2-yl)isoxazole-5-carboxylate (3.9 g, 16.5 mmol), NBS (3.5 g, 19.7 mmol), and benzoyl peroxide (0.4 g, 1.65 mmol) were added to 100 mL of carbon tetrachloride and the mixture was refluxed for 16 h. The reaction mixture was filtered and the filtrate was removed in vacuo. The residue, containing both unreacted starting material and the title compound, was used in the next reaction without purification. MS: (+) m/z 316, 318 (M+1, 79Br/81Br).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was removed in vacuo
  4. additionThe residue, containing
  5. customthe title compound, was used in the next reaction without purification

Sources & evidence

ORD record
ord-fb8a2bc21d8d487dbb7e1948ce1e171d
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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