1-Bromo-4-methyl-2-pentanone → 2-(4-methyl-2-oxopentyl)-1H-isoindole-1,3(2H)-dione

HRID 1670528Notes

Reaction equation

HRID 1670528 reaction equation
Br[CH2:2][C:3](=[O:8])[CH2:4][CH:5]([CH3:7])[CH3:6].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>C1(C)C=CC=CC=1>[CH3:6][CH:5]([CH3:7])[CH2:4][C:3](=[O:8])[CH2:2][N:13]1[C:9](=[O:19])[C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]1=[O:14]

Participants

4

Reactant 2

HCID 110844641-Bromo-4-methyl-2-pentanoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 70388412-(4-methyl-2-oxopentyl)-1H-isoindole-1,3(2H)-dioneYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 1-bromo-4-methyl-2-pentanone (11.0 g, 61.4 mmol) and potassium phthalimide (11.9 g, 64.5 mmol) in toluene (60 mL) at room temperature under a nitrogen atmosphere. Heat the mixture to 100° C. and stir for 16 h. Cool the resulting slurry to room temperature, filter off solids, and concentrate the filtrate in vacuo to a solid. Purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (1:1) to obtain the desired intermediate (3.6 g, 24%). MS (ES+) m/z: 246.3 (M+H)+.

Workup

  1. temperatureCool the resulting slurry to room temperature
  2. filtrationfilter off solids
  3. concentrationconcentrate the filtrate in vacuo to a solid
  4. customPurify the residue by chromatography on silica gel (40 g)
  5. washeluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-c5a8835debb8401da040f4f53c22ff11
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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