Water → HCID 23021557, compound

HRID 501788Notes

Reaction equation

HRID 501788 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([O:9][CH2:10][O:11][CH3:12])=[N:7][O:8][C:4]=2[CH:3]=1.[Br:15]N1C(=O)CCC1=O.C(OCC)(=O)C.O>C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:15][CH2:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([O:9][CH2:10][O:11][CH3:12])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 23021550HCID 23021550, compound

Product 1

HCID 23021557HCID 23021557, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 241BenzeneSolvent

Procedure

20.0 g of methoxymethyl 6-methyl-1,2-benzisoxazol-3-yl ether was dissolved in 200 mL of benzene, to which 20.3 g of N-bromosuccinimide and 1.7 g of 2,2′-azobisisobutyronitrile were successively added at room temperature, and this mixture was stirred for 30 minutes while heating it under reflux. The reaction mixture was cooled to room temperature, and added to a mixture of ethyl acetate and water, and then the organic phase was separated therefrom. After the resultant organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 28.5 g of 6-(bromomethyl)-3-(methoxymethoxy)-1,2-benzisoxazole as light brown oil.

Workup

  1. additionwere successively added at room temperature
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. customthe organic phase was separated
  5. washAfter the resultant organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate
  6. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-e02bdaf30f8d47e9844db6161de6529e
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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