Benzoyl Peroxide → 5-(4-(Bromomethyl)phenyl)isoxazole

HRID 1166294Notes

Reaction equation

HRID 1166294 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][N:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][N:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2700155-(P-Tolyl)isoxazole

Product 1

HCID 229975455-(4-(Bromomethyl)phenyl)isoxazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Bisbenzoyl peroxide (560 mg, 0.232 mmol) is added to a solution of 2.17 g (13.65 mmol) of 5-(4-methyl-phenyl)-isoxazole (Lin, Y. -i.; Lang, Jr., S. A. J. Org. Chem. 1980, 45, 4857) and N-bromosuccinimide (2.43 g, 13.65 mmol) in 64 mL of CCl4, and the reaction mixture is heated at reflux overnight. The reaction mixture is then concentrated in vacuo, and the product is purified by chromatography on silica gel (20% EtOAC/hexane, Rf=0.6) to yield 5-(4-bromomethyl-phenyl)-isoxazole. 1H NMR (250 MHz., CDCl3) δ 8.30 (d, 1H), 7.73 (d, 2H), 7.45 (d, 2H), 6.51 (d, 1H), 4.50 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. customthe product is purified by chromatography on silica gel (20% EtOAC/hexane, Rf=0.6)

Sources & evidence

ORD record
ord-63b88f5e053a47188f22d1cb14d9ce3f
Source dataset
uspto-grants-2003_09
Patent number
US06613782B2

Reaction notes

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