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

HRID 1087953Notes

Reaction equation

HRID 1087953 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>[Br:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:2])[O:3]1

Participants

4

Reactant 2

HCID 6885PhthalideHCID 67184N-bromobutanimide

Product 1

HCID 962181(3H)-Isobenzofuranone, 3-bromo-Yield 97%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of phthalide (7.5 g, 56 mmol) and N-bromosuccinimide (10 g, 55.5 mmol) in CCl4 (150 mL) was heated at reflux for 3 hours (reaction checked by TLC). The mixture was filtered hot and the filtrate was evaporated to dryness to yield the crude title compound (11.15 g, 97%). It was used as such in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. custom(reaction checked by TLC)
  4. filtrationThe mixture was filtered hot
  5. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-1390377fc09743a18662ab98887d9ba9
Source dataset
uspto-grants-1990_10
Patent number
US04960902

Reaction notes

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