Dimethylformamide → 5-(4-Fluoro-phenoxy)-isoindole-1,3-dione

HRID 523697

Reaction equation

HRID 523697 reaction equation
[N+]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7]2=[O:14])([O-])=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:13])[NH:8][C:7]3=[O:14])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 69694-NitrophthalimideHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 667126295-(4-Fluoro-phenoxy)-isoindole-1,3-dioneYield 18.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-Nitro-isoindole-1,3-dione (177 g, 0.904 mol), 4-fluoro-phenol (128 g, 1.13 mol), K2CO3 (419 g, 3 mol) and DMF (2 l) was refluxed with stirring for 3 h before the mixture was poured into water (12 l) with stirring. The precipitate formed was isolated by vacuum filtration, washed with water (8 l) and dried in vacuo at 70° C. to give the title compound as a tan powder (43.2 g); 1H NMR (CDCl3) δ=7.79 (d, 1H), 7.57 (br s, 1H), 7.01 to 7.29 (m, 6H).

Workup

  1. temperaturewas refluxed
  2. stirringwith stirring
  3. customThe precipitate formed
  4. customwas isolated by vacuum filtration
  5. washwashed with water (8 l)
  6. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-15d359107eb6498fbb5125659c94f977
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Linked notes

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