Reaktion #306936

Reaktionsgleichung

5-iodoisatin

magnesium

iodine

NH4Cl

2-bromo-1-ethoxybenzene

2-bromo-1-ethoxybenzene

→

product

3-(2-Ethoxyphenyl)-3-hydroxy-5-iodoindol-2-one

Lösungsmittel

tetrahydrofuran

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwere heated until the reaction
2. 2
   workup.ADDITIONwere slowly added dropwise to the boiling solution in such a way that the reaction
3. 3
   workup.STIRRINGwith stirring
4. 4
   ExtraktionThis aqueous phase was extracted several times with ethyl acetate
5. 5
   Waschenthe combined aqueous phase was washed four times with water
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigeresulting in the product as a crystalline precipitate

Vorschrift

4 g (164 mMol) of magnesium turnings and 5% of the total amount of 2-bromo-1-ethoxybenzene were put into 20 ml of ether and, after addition of a little iodine, were heated until the reaction started. 33.1 g (165 mMol) of 2-bromo-1-ethoxybenzene dissolved in 100 ml of ether were slowly added dropwise to the boiling solution in such a way that the reaction continued with gentle boiling. Then, while cooling slightly to 20° C., 15 g (54.9 mMol) of 5-iodoisatin in 400 ml of anhydrous tetrahydrofuran were added dropwise. The mixture was then stirred at room temperature for 2 h. The reaction solution was poured into an aqueous NH4Cl solution with stirring. This aqueous phase was extracted several times with ethyl acetate, and the combined aqueous phase was washed four times with water, dried and concentrated in vacuo, resulting in the product as a crystalline precipitate. 19.2 g of the product were obtained.

Quelle