N-bromobutanimide → HCID 12298540, compound

HRID 2268852

Reaction equation

HRID 2268852 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][O:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[Br:13]N1C(=O)CCC1=O.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9](=[O:12])[O:8]1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 3305396-MethoxyphthalideHCID 11229634Benzyl Peroxide

Product 1

HCID 12298540HCID 12298540, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

6-Methoxy-3H-isobenzofuran-1-one (35.28 g, 0.215 mole), prepared as described in example 34, suspended in CCl4 (350 ml) under N2 was added with N-bromosuccinimide (40 g, 0.225 mole) and benzyl peroxide in catalytic amount, then slowly brought to reflux. After 2.5 hours the heating was stopped and the mixture was left to stand overnight at room temperature. Further catalyst was added and the mixture was heated for further 3.5 hours. The mixture was cooled in ice, filtered over celite washing well with CCl4 and dried to give 41 g of the title compound (yield: 78%).

Workup

  1. temperatureto reflux
  2. waitthe mixture was left
  3. waitto stand overnight at room temperature
  4. additionFurther catalyst was added
  5. temperaturethe mixture was heated for further 3.5 hours
  6. temperatureThe mixture was cooled in ice
  7. filtrationfiltered over celite
  8. washwashing well with CCl4
  9. customdried

Sources & evidence

ORD record
ord-35147d22878c47b6b8105aa2b1b72661
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Linked notes

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