Potassium Carbonate → 2-(3-Bromo-2-methylphenyl)isoindoline

HRID 1811019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811019
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([N:5]2[CH2:18][C:13]3[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 119191,2-Bis(chloromethyl)benzeneHCID 1235383-Bromo-o-toluidine

Produkt 1

HCID 593751132-(3-Bromo-2-methylphenyl)isoindolineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 3-bromo-2-methylaniline (372 mg, 2.00 mmol), 1,2-bis(chloromethyl)benzene (385 mg, 2.20 mmol), and potassium carbonate (304 mg, 2.20 mmol) in water (2 mL) was heated via microwave irradiation in a sealed tube at 120° C. for 25 min. The mixture was extracted with EtOAc and the organic phase was washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 30:70 EtOAc-hexane) to provide 2-(3-bromo-2-methylphenyl)isoindoline as a light yellow oil (360 mg, 63%). Mass spectrum m/z 288, 290 (M+H)+.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (
  6. washeluting with a gradient from hexane to 30:70 EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4728f210ece94747907e1fd65cfe3822
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362065B2

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