N-Hydroxyphthalimide → N-Benzyloxyphthalimide

HRID 1959624Notes

Reaction equation

HRID 1959624 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24](OC)=[CH:23][CH:22]=1>CS(C)=O>[CH2:20]([O:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 10796Cesium carbonateHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 255292N-BenzyloxyphthalimideYield 58%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-hydroxyisoindoline-1,3-dione (1.0 g, 6.13 mmol) in DMSO (10 mL) was added Cs2CO3 (1.997 g, 6.13 mmol). The resulting mixture was stirred at it for 30 min. 1-bromomethyl 4-methoxy-benzene (0.88 mL, 6.13 mmol) was then added dropwise. After stirring at 50° C. overnight, the reaction mixture was quenched with NH4Cl (aq), extracted with EtOAc, washed with NH4Cl (aq), dried over Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by silica gel column with gradient hexanes:EtOAc to give 2-(benzyloxy)isoindoline-1,3-dione as a white solid (0.9 g, 49%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.85 (s, 4H), 7.42 (d, 2H), 6.94 (d, 2H), 5.08 (s, 2H), 3.75 (s, 3H).

Workup

  1. stirringAfter stirring at 50° C. overnight
  2. customthe reaction mixture was quenched with NH4Cl (aq)
  3. extractionextracted with EtOAc
  4. washwashed with NH4Cl (aq)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product, which
  9. customwas purified by silica gel column with gradient hexanes

Sources & evidence

ORD record
ord-26e701f92f0441e6b567b6b2d37d0d09
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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