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

HRID 1689761Notes

Reaction equation

HRID 1689761 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 washed with 0.2 N HCl. The organic layer is separated, dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound as an oil.

Workup

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

Sources & evidence

ORD record
ord-edade6575e5146b2a074f20c85ea4893
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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