N-Hydroxyphthalimide → 2-[(Perfluorophenyl)methoxy]isoindoline-1,3-dione

HRID 1632246Notes

Reaction equation

HRID 1632246 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].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[C:25]([CH2:26]Br)=[C:24]([F:28])[C:23]([F:29])=[C:22]([F:30])[C:21]=1[F:31]>C(COC)OC.CS(C)=O>[F:19][C:20]1[C:25]([CH2:26][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])=[C:24]([F:28])[C:23]([F:29])=[C:22]([F:30])[C:21]=1[F:31]

Participants

6

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 74484Pentafluorobenzyl bromide

Product 1

HCID 136577462-[(Perfluorophenyl)methoxy]isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

N-hydroxyphthalimide (8.15 g, 0.05 mol) was dissolved in a mixture of dry dimethoxyethane (40 ml) and dry dimethyl sulphoxide (10 ml). To this solution was added, in one portion, potassium carbonate (3.46 g, 0.05 mol). An orange suspension resulted. The pentafluorobenzyl bromide (10.8 g, 0.05 mol) in dry dimethoxyethane (10 ml) was added dropwise over 1 h at room temperature. The reaction mixture was stirred at room temperature for 64 h and then quenched by pouring into water (1 l). The resulting slurry was filtered, the crystals washed with water and dried in vacuo to give N-(pentafluorobenzyloxy)phthalimide as white crystals (15.9)g.

Workup

  1. customAn orange suspension resulted
  2. customquenched
  3. additionby pouring into water (1 l)
  4. filtrationThe resulting slurry was filtered
  5. washthe crystals washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-87b9c9e0ca2a496ab3a802be3a00142f
Source dataset
uspto-grants-1984_10
Patent number
US04474815

Reaction notes

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