Water → 5-bromo-3-hydroxy-3H-isobenzofuran-1-one

HRID 978650Notes

Reaction equation

HRID 978650 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2.BrN1C(=[O:18])CCC1=O.O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH:5]2[OH:18]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 6031445-Bromophthalide

Product 1

HCID 142348425-bromo-3-hydroxy-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 13.3 gm 5-bromophthalide and 12.7 gm N-bromosuccinimide in 480 ml carbon tetrachloride was irradiated with a tungsten floor lamp and refluxed for 3 hours. The reaction was followed by NMR. The succinimide was filtered off and the cake washed with carbon tetrachloride. The solvent was removed in vacuo leaving a residue of 19.2 gm, to which was added 100 ml water. This mixture was refluxed with stirring for 4 hours, then the mixture was cooled and the product filtered off, washed neutral with water and dried. Wt=9.9 gm.

Workup

  1. customwas irradiated with a tungsten floor lamp
  2. temperaturerefluxed for 3 hours
  3. filtrationThe succinimide was filtered off
  4. washthe cake washed with carbon tetrachloride
  5. customThe solvent was removed in vacuo
  6. customleaving a residue of 19.2 gm
  7. temperatureThis mixture was refluxed
  8. temperaturethe mixture was cooled
  9. filtrationthe product filtered off
  10. washwashed neutral with water
  11. customdried

Sources & evidence

ORD record
ord-264c6c93ae164fae96da951fa529bfc6
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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