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

HRID 2230232Notes

Reaction equation

HRID 2230232 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) δ8.30 (d, 1 H), 7.73 (d, 2 H), 7.45 (d, 2 H), 6.51 (d, 1 H), 4.50 (s, 2 H).

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-34b65f06e4f94a4aaef9a12476dd2bb3
Source dataset
uspto-grants-2002_07
Patent number
US06423727B1

Reaction notes

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