Bromobenzene → 7-Chloro-3-hydroxy-3-phenyl-2-indolinone

HRID 329271Notes

Reaction equation

HRID 329271 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16](=[O:19])[C:15]2=[O:20]>O1CCCC1.[OH-].[Na+]>[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16](=[O:19])[C:15]2([OH:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 3441357-ChloroisatinHCID 5462224Magnesium

Product 1

HCID 214394277-Chloro-3-hydroxy-3-phenyl-2-indolinone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A Grignard reagent prepared from 62 g. magnesium, 400 g. bromobenzene in two liters tetrahydrofuran (THF) is added to 181 g. (1.0 mole) 7-chloroisatin (1a) in two liters THF at a rate to keep a gentle reflux. After three hours of reflux, the reaction is cooled and decomposed with 350 ml. saturated ammonium chloride, filtered, and the THF stripped to give a dark oil. The oil is dissolved in aqueous sodium hydroxide and precipitated with hydrochloric acid. Recrystallization from aqueous ethanol gives 7-chloro-3-hydroxy-3-phenyl-2-indolinone, m.p. 154°-156°.

Workup

  1. temperatureAfter three hours of reflux
  2. temperaturethe reaction is cooled
  3. filtrationsaturated ammonium chloride, filtered
  4. customto give a dark oil
  5. customprecipitated with hydrochloric acid
  6. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-98ca840e9e704ec283dd9b749a35a7e9
Source dataset
uspto-grants-1977_04
Patent number
US04020179

Reaction notes

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