Potassium Carbonate → (5-Bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid methyl ester

HRID 1618230Notes

Reaction equation

HRID 1618230 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC(C)=O>[CH3:24][O:23][C:21](=[O:22])[CH2:20][N:8]1[C:9](=[O:10])[C:4]2[C:5](=[CH:11][CH:12]=[C:2]([Br:1])[CH:3]=2)[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 2360184-Bromophthalimide

Product 1

HCID 30374730(5-Bromo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

50.3 g of 4-bromophthalimide, 92.0 g of potassium carbonate, and 24.5 ml of methyl bromoacetate were added to 888 ml of acetone. The resultant mixture was heated to reflux temperature for 24 h, and then cooled to room temperature. The mixture was filtered through a fine glass frit to remove all solid material, and the solution was then concentrated under vacuum to provide 66 g of the desired product, a white solid; 1H NMR (CDCl3): δ=3.76 (s, 3H), 4.43 (s, 2H), 7.71-7.75 (m, 1H), 7.85-7.90 (dd, 1H), 8.00 (m, 1H).

Workup

  1. temperatureto reflux temperature for 24 h
  2. filtrationThe mixture was filtered through a fine glass frit
  3. customto remove all solid material
  4. concentrationthe solution was then concentrated under vacuum

Sources & evidence

ORD record
ord-0953eac21fe2468e97c8c7d7e1cd9dd1
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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