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

HRID 1593396

反応式

HRID 1593396 の反応式
[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]

参加物

8

反応物 4

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

生成物 2

HCID 219058993-Hydroxy-3-(2-methoxyphenyl)-5-trifluoromethoxy-1,3-dihydro-2H-indol-2-one収率 76.3%HCID 178489560HCID 178489560、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3564bb8751494add800b81fcea59bebe
出典データセット
uspto-grants-2007_11
特許番号
US07297692B2

関連ノート

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