Reaktion #59631

Reaktionsgleichung

5,6-dichloro-1H-indole-2,3-dione

1-bromo-2-methoxybenzene

magnesium

iodine

→

expected product

Ausbeute 74.0%

5,6-Dichloro-3-hydroxy-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

Ausbeute 74.0%

Lösungsmittel

THF

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reflux being maintained once it
2. 2
   workup.ADDITIONAt the end of the addition
3. 3
   Temperaturthe mixture is refluxed for 2 hours
4. 4
   workup.ADDITIONis then added
5. 5
   Temperaturthe mixture is refluxed for 30 minutes
6. 6
   Extraktionextracted with EtOAc
7. 7
   Trocknenthe organic phase is dried over Na2SO4
8. 8
   Sonstigethe solvent is evaporated off under vacuum
9. 9
   Sonstigethe precipitate formed
10. 10
    Filtrationis spin-filtered off
11. 11
    Waschenwashed with ether

Vorschrift

5.57 g of 1-bromo-2-methoxybenzene are added dropwise to a suspension of 0.72 g of magnesium in 15 ml of ether containing a few crystals of iodine, the reflux being maintained once it has started. At the end of the addition, the mixture is refluxed for 2 hours. A suspension of 2.7 g of 5,6-dichloro-1H-indole-2,3-dione in 30 ml of THF is then added and the mixture is refluxed for 30 minutes. After cooling to RT, the reaction mixture is poured into a water/ice/-concentrated HCl mixture and extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is slurried in hot iso ether and the precipitate formed is spin-filtered off and washed with ether. 3 g of the expected product are obtained.

Quelle