Phthalide → 1(3H)-Isobenzofuranone, 3-bromo-

HRID 437180Notes

Reaction equation

HRID 437180 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH:7]1[CH:6]=[C:5]2[CH:4]([Br:11])[O:3][C:1](=[O:2])[C:10]2=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6885PhthalideHCID 67184N-bromobutanimide

Product 1

HCID 962181(3H)-Isobenzofuranone, 3-bromo-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 1.34 g of phthalide and 1.78 g of N-bromo-succinimide in 100 ml of dry carbon tetrachloride is irradiated with an ultraviolet lamp for 30 minutes. The suspension becomes clear and then a precipitation of succinimide occurs. The reaction mixture is cooled and washed with cold, dilute sodium bicarbonate and water. Concentration of the carbon tetrachloride solution affords a solid, which on recrystallization from ether-hexane affords the title compound, mp 75° - 76° C.

Workup

  1. customis irradiated with an ultraviolet lamp for 30 minutes
  2. customa precipitation of succinimide
  3. temperatureThe reaction mixture is cooled
  4. washwashed with cold, dilute sodium bicarbonate and water
  5. customConcentration of the carbon tetrachloride solution affords a solid, which
  6. customon recrystallization from ether-hexane

Sources & evidence

ORD record
ord-8dd437baf6bf41c19e4b7b41afa4085e
Source dataset
uspto-grants-1977_06
Patent number
US04029810

Reaction notes

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