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

HRID 2388182Notes

Reaction equation

HRID 2388182 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:11][N:10]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:27])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:14][C:13]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[N:10][O:11][C:12]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67530223Ethyl 3-(4-methoxyphenyl)-4-methylisoxazole-5-carboxylate

Product 1

HCID 67529710Ethyl 4-(bromomethyl)-3-(4-methoxyphenyl)isoxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 3-(4-methoxyphenyl)-4-methylisoxazole-5-carboxylate (12.4 g, 47.5 mmol), NBS (10.1 g, 57.0 mmol), and benzoyl peroxide (1.15 g, 4.75 mmol) were added to 250 mL of carbon tetrachloride and the mixture was refluxed for 16 h. The reaction mixture was filtered and the filtrate was removed in vacuo to give a brown solid, which was used in the next reaction without purification. MS: (+) m/z 340.35, 342.33 (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. customto give a brown solid, which
  5. customwas used in the next reaction without purification

Sources & evidence

ORD record
ord-3d8f7b6b09b949a99b7cb313e6647174
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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