N-bromobutanimide → 3-(4-(Bromomethyl)phenyl)isoxazole

HRID 2224249Notes

Reaction equation

HRID 2224249 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 114805953-p-Tolylisoxazole

Product 1

HCID 186634113-(4-(Bromomethyl)phenyl)isoxazoleYield 20.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-(4-methylphenyl)isoxazole (prepared using literature methods) (1.95 g, 12.25 mmol) in carbon tetrachloride (60 mL), N-bromosuccinimide (2.18 g, 12.25 mmol) and benzoyl peroxide (0.059 g, 0.245 mmol) were added and the mixture refluxed for 1 h. The reaction mixture was then cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography eluting with hexanes/EtOAc to give the title compound, 3-(4-(bromomethyl)phenyl)isoxazole, (0.6 g) as a white solid. 1H NMR (CDCl3): δ 8.48 (d, J=1.6 Hz, 1H), 7.83 (d, J=8.2 Hz, 2H), 7.50 (d, J=8.2 Hz, 2H), 6.67 (d, J=1.6 Hz, 1H), 4.53 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-4b8092ce4a9648959aadb52392e92052
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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