N-Hydroxyphthalimide → Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

HRID 414865Notes

Reaction equation

HRID 414865 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:18]([O:17][C:15]([CH2:14][O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetateYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (200 ml) ar dissolved 24.5 g (0.15 mole) of N-hydroxyphthalimide and 29.3 g (0.15 mole) of tert-butyl bromoacetate, and 20.7 g (0.15 mole) of powdered potassium carbonate is added to the solution under ice-cooling with stirring. The reaction solution is stirred under ice-cooling for 30 minutes and then at room temperature for 20 hours, and poured into 2 l of ice cold water. The crystals that separate out are recovered by filtration, washed with 1 l of water and 500 ml of hexane successively and dried under reduced pressure at 40° C. to give 39.7 g (95.5%) of N-(tert-butoxycarbonylmethoxy)phthalimide as colorless crystals. This product is to be used in the subsequent reaction, and part of this product, when recrystallized from etyyl acetate-n-hexane (1:2), exhibits a melting point of 145°-146° C.

Workup

  1. additionis added to the solution under ice-
  2. temperaturecooling
  3. stirringThe reaction solution is stirred under ice-
  4. temperaturecooling for 30 minutes
  5. customThe crystals that separate out
  6. filtrationare recovered by filtration
  7. washwashed with 1 l of water and 500 ml of hexane successively
  8. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-80845183df8342b7adabc13771c26556
Source dataset
uspto-grants-1988_12
Patent number
US04794108

Reaction notes

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