1,3-Isobenzofurandione, 5-fluoro- → 2-(3-Bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dione

HRID 661824

Reaktionsgleichung

Reaktionsgleichung von HRID 661824
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[O:15][C:14]2=O>C(O)(=O)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([N:5]2[C:14](=[O:15])[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([F:10])[CH:12]=3)[C:16]2=[O:20])[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 675721,3-Isobenzofurandione, 5-fluoro-HCID 1235383-Bromo-o-toluidine

Produkt 1

HCID 593750082-(3-Bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dioneAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-bromo-2-methylaniline (200 mg, 1.075 mmol) and 5-fluoroisobenzofuran-1,3-dione (179 mg, 1.075 mmol) in acetic acid (2 mL) was heated at 100° C. for 4.5 h. The mixture was concentrated and the residue was purified by column chromatography (eluting with a gradient from hexane to 60:40 hexane-EtOAc) to give 2-(3-bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dione as a white solid (235 mg, 59%). Mass spectrum m/z 334, 336 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography (
  3. washeluting with a gradient from hexane to 60:40 hexane-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-26ee4db9b11f41bea0c18d0f1a457f6e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084620B2

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