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

HRID 2224247Notes

Reaction equation

HRID 2224247 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=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

To a solution of 5-(4-methylphenyl)isoxazole (4.0 g, 25.13 mmol) in carbon tetrachloride (125 mL), N-bromosuccinimide (4.47 g, 25.13 mmol) and benzoyl peroxide (0.12 g, 0.50 mmol) were added. The resulting mixture refluxed for 1 h. After this time, the raction mixture was then cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by silica gel chromatography eluting with hexanes/EtOAc to give the title compound, 5-(4-(bromomethyl)phenyl)isoxazole, 4.2 g as an off-white solid. 1H NMR (CDCl3): δ 8.30 (d, J=2.2 Hz, 1H), 7.78 (d, J=8.3 Hz, 2H), 7.50 (d, J=8.3 Hz, 2H), 6.54 (d, J=1.7 Hz, 1H), 4.51 (s, 2H).

Workup

  1. temperatureThe resulting mixture refluxed for 1 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with hexanes/EtOAc

Sources & evidence

ORD record
ord-bdad59050624420faea5c5aff8ec1051
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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