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

HRID 2060480Notes

Reaction equation

HRID 2060480 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-e7ff3847dde6486ab3f9cbc050229cdf
Source dataset
uspto-grants-2012_10
Patent number
US08278325B2

Reaction notes

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