Water → 3-Hydroxy-4,6-dichloro-1,3-dihydro-3-(4-trifluoromethylphenyl)indol-2-one

HRID 219762

反応式

HRID 219762 の反応式
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]2[C:15]=1[C:16](=[O:25])[C:17](=[O:24])[NH:18]2.O>C(OCC)C.C1COCC1>[OH:25][C:16]1([C:3]2[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=2)[C:15]2[C:19](=[CH:20][C:21]([Cl:23])=[CH:22][C:14]=2[Cl:13])[NH:18][C:17]1=[O:24]

参加物

7

反応物 4

HCID 962WaterHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 2519084,6-DichloroisatinHCID 5462224Magnesium

生成物 1

HCID 666026703-Hydroxy-4,6-dichloro-1,3-dihydro-3-(4-trifluoromethylphenyl)indol-2-one

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

1.8 g of Grignard magnesium are placed in 19 ml of anhydrous ethyl ether in a round-bottomed flask equipped with a mechanical stirrer, and under a stream of nitrogen. A mixture of 8.9 ml of 4-bromotrifluoromethylbenzene in 46 ml of anhydrous ethyl ether is then added. The mixture is stirred for one hour, followed by addition of a solution of 5.7 g of 4,6-dichloro-1H-indole-2,3-dione in 100 ml of anhydrous THF. The mixture is stirred at room temperature for 4 hours 30 minutes. Water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is separated out and dried over Na2SO4, filtered and evaporated under vacuum. The residue is taken up in ethyl acetate and washed with 1N sodium hydroxide solution. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. The solid is taken up in ethyl ether and filtered off. 4.7 g of expected product are obtained.

後処理

  1. customequipped with a mechanical stirrer
  2. additionis then added
  3. stirringThe mixture is stirred at room temperature for 4 hours 30 minutes
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. customThe organic phase is separated out
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. washwashed with 1N sodium hydroxide solution
  10. dry with materialThe organic phase is dried over Na2SO4
  11. filtrationfiltered
  12. customevaporated under vacuum
  13. filtrationfiltered off

出典と根拠

ORDレコード
ord-15e2988c599d4d829b0be32d5a2db277
出典データセット
uspto-grants-2012_06
特許番号
US08202871B2

関連ノート

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