Phthalic Anhydride → 2-(3-Bromophenyl)-1H-isoindole-1,3(2H)-dione

HRID 1385322Notes

Reaction equation

HRID 1385322 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]1(=O)[O:14][C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[C:12](=[O:13])[C:11]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]3[C:9]2=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 115623-Bromoaniline

Product 1

HCID 45355142-(3-Bromophenyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirring slurry of 3-bromoaniline (3.00 g, 17.44 mmol), phthalic anhydride (2.58 g, 17.44 mmol), and toluene (45 ml) was heated under reflux, using a Dean-Stark apparatus, at 140° C. (oil bath temperature) for 24 h. After cooling to ambient temperature, the solution was concentrated by rotary evaporation. The resulting off-white solid was purified by column chromatography on silica gel (150 g, Merck 70-230 mesh) eluting with CHCl3-acetone (9:1, v/v) to collect unreacted 3-bromoaniline (Rf 0.61) and phthalic anhydride (Rf 0.43). Elution with CHCl3-methanol (9:1, v/v) gave the product (Rf 0.38). Selected fractions containing the product were combined and concentrated by rotary evaporation to give 1.53 g of an off-white to light-beige solid. Impure fractions were combined and concentrated by rotary evaporation. The resulting white solid was dissolved in a mixture of CHCl3, acetone, and methanol and re-chromatographed on silica gel (150 g). Elution with CHCl3 removed impurities; the product was then eluted with CHCl3-acetone (4:1, v/v). Selected fractions were combined, concentrated by rotary evaporation, and vacuum dried for 16 h to give 1.41 g of an off-white to light-beige solid, mp 176-179° C., bringing the total yield to 2.94 g (55.8%).

Workup

  1. temperatureunder reflux
  2. concentrationthe solution was concentrated by rotary evaporation
  3. customThe resulting off-white solid was purified by column chromatography on silica gel (150 g, Merck 70-230 mesh)
  4. washeluting with CHCl3-acetone (9:1
  5. customv/v) to collect unreacted 3-bromoaniline (Rf 0.61) and phthalic anhydride (Rf 0.43)
  6. washElution with CHCl3-methanol (9:1
  7. customv/v) gave the product (Rf 0.38)
  8. additionSelected fractions containing the product
  9. concentrationconcentrated by rotary evaporation
  10. customto give 1.53 g of an off-white to light-beige solid
  11. concentrationconcentrated by rotary evaporation
  12. dissolutionThe resulting white solid was dissolved in a mixture of CHCl3, acetone, and methanol
  13. customre-chromatographed on silica gel (150 g)
  14. washElution with CHCl3 removed impurities
  15. washthe product was then eluted with CHCl3-acetone (4:1, v/v)
  16. concentrationconcentrated by rotary evaporation, and vacuum
  17. customdried for 16 h
  18. customto give 1.41 g of an off-white to light-beige solid, mp 176-179° C.
  19. customtotal yield to 2.94 g (55.8%)

Sources & evidence

ORD record
ord-385f4c90d62648e087276ccb9ab737ce
Source dataset
uspto-grants-2001_07
Patent number
US06262124B1

Reaction notes

Loading…