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

HRID 1593396

Reaktionsgleichung

Reaktionsgleichung von HRID 1593396
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[F:11][C:12]([F:26])([F:25])[O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[C:17]2=[O:24].[NH4+].[Cl-]>CCOCC.C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][CH:20]=[CH:21][C:22]=1[Mg:1][Br:2].[OH:24][C:17]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[O:9][CH3:10])[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([O:13][C:12]([F:11])([F:25])[F:26])[CH:15]=2)[NH:19][C:18]1=[O:23]

Komponenten

8

Edukt 4

HCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 27327525-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dioneHCID 5462224Magnesium

Produkt 2

HCID 219058993-Hydroxy-3-(2-methoxyphenyl)-5-trifluoromethoxy-1,3-dihydro-2H-indol-2-oneAusbeute 76,3 %HCID 178489560HCID 178489560, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-methoxyphenylmagnesium bromide is prepared from 1.9 g of magnesium in 4 ml of ether and from a solution of 14.54 g of 1-bromo-2-methoxybenzene in 21 ml of ether. This solution is added drop wise, under an argon atmosphere, to a mixture of 5 g of 5-trifluoromethoxy-1H-indole-2,3-dione in 26 ml of THF, cooled beforehand in an ice bath, and then heated at the reflux point of the ether for 1 hour 30 minutes and 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.

Aufarbeitung

  1. additionThis solution is added drop wise
  2. temperaturecooled
  3. custombeforehand in an ice bath
  4. extractionextracted with EtOAc
  5. washthe organic phase is washed with 5% K2CO3 solution, with water and with saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated off under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3564bb8751494add800b81fcea59bebe
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297692B2

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