Phosphorus tribromide → 4-Bromomethyl-3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazole

HRID 250223Notes

Reaction equation

HRID 250223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1.P(Br)(Br)[Br:20]>C1COCC1.CCOC(C)=O>[Br:20][CH2:14][C:13]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[N:10][O:11][C:12]=1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanol

Product 1

HCID 669064404-Bromomethyl-3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-yl]-methanol (1.14 g, 4 mmol) in THF (20 mL) is added PBr3 (0.76 mL, 8 mmol). The reaction mixture is stirred at reflux for 30 minutes. The reaction mixture is diluted with EtOAc and is washed with 0.2 N HCl. The organic layer is separated, dried (MgSO4), filtered, and concentrated to give the title compound as an oil.

Workup

  1. temperatureat reflux for 30 minutes
  2. washis washed with 0.2 N HCl
  3. customThe organic layer is separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34863f845a6e4400b25b1ad6be7d4b50
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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