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

HRID 1593396

반응식

HRID 1593396 반응식
[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]

참가 물질

8

반응물 4

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

생성물 2

HCID 219058993-Hydroxy-3-(2-methoxyphenyl)-5-trifluoromethoxy-1,3-dihydro-2H-indol-2-one수율 76.3%HCID 178489560HCID 178489560, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3564bb8751494add800b81fcea59bebe
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297692B2

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