Bromopinacolone → 2-(3,3-Dimethyl-2-oxobutyl)-1H-isoindole-1,3(2H)-dione

HRID 1870084Notes

Reaction equation

HRID 1870084 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[CH2:14][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 21642BromopinacoloneHCID 24194345Phthalimide potassium salt

Product 1

HCID 3043232-(3,3-Dimethyl-2-oxobutyl)-1H-isoindole-1,3(2H)-dioneYield 76.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium phthalimide (82.86 g, 0.447 mol) is added to a stirred solution of bromopinacolone (80.10 g, 0.447 mol) in toluene (300 ml). The-suspension is refluxed for 19 h, cooled, and then the precipitate is filtered off and discarded. The filtrate is cooled in an ice-bath and treated with petroleum ether (550 ml). The resulting precipitate is collected by filtration. The mother liquor is reduced to circa 100 ml by evaporation in vacuo, and a further quantity of precipitate which forms is collected by filtration and combined with the first crop, giving 2-(3,3-dimethyl-2-oxo-butyl)-isoindole-1,3-dione (total yield 83.5 g, 76%) as colourless crystals, m.p. 96-99° C.

Workup

  1. temperatureThe-suspension is refluxed for 19 h
  2. temperaturecooled
  3. filtrationthe precipitate is filtered off
  4. temperatureThe filtrate is cooled in an ice-bath
  5. additiontreated with petroleum ether (550 ml)
  6. filtrationThe resulting precipitate is collected by filtration
  7. customThe mother liquor is reduced to circa 100 ml by evaporation in vacuo
  8. filtrationa further quantity of precipitate which forms is collected by filtration

Sources & evidence

ORD record
ord-bd5e522a2f604026ab60fef54411968d
Source dataset
uspto-grants-2000_08
Patent number
US06096688

Reaction notes

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