Reaktion #59630

Reaktionsgleichung

5-trifluoromethoxy-1H-indole-2,3-dione

NH4Cl

1-bromo-2-methoxybenzene

magnesium

→

2-methoxyphenylmagnesium bromide

expected product

Ausbeute 76.3%

3-Hydroxy-3-(2-methoxyphenyl)-5-trifluoromethoxy-1,3-dihydro-2H-indol-2-one

Ausbeute 76.3%

Lösungsmittel

THF

ether

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprecooled on an ice bath
2. 2
   Extraktionextracted with EtOAc
3. 3
   Waschenthe organic phase is washed with 5% K2CO3 solution, with water and with saturated NaCl solution
4. 4
   Trocknendried over Na2SO4
5. 5
   Sonstigethe solvent is evaporated off under vacuum

Vorschrift

A solution of 2-methoxyphenylmagnesium bromide is prepared starting with 1.9 g of magnesium in 4 ml of ether and a solution of 14.54 g of 1-bromo-2-methoxybenzene in 21 ml of ether. This solution is added dropwise, under an argon atmosphere, to a mixture of 5 g of 5-trifluoromethoxy-1H-indole-2,3-dione in 26 ml of THF, precooled on an ice bath, the resulting mixture is then heated at the reflux temperature of the ether for 1 hour 30 minutes and is allowed to cool to RT. The reaction mixture is poured slowly into saturated NH4Cl solution and extracted with EtOAc, the organic phase is washed with 5% K2CO3 solution, with water and with saturated NaCl solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. 2.8 g of the expected product are obtained.

Quelle