Iodine → 5,6-Dichloro-3-hydroxy-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

HRID 1243317

反応式

HRID 1243317 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].II.[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[Cl:23])[NH:19][C:18](=[O:24])[C:17]2=[O:25]>CCOCC.C1COCC1>[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[Cl:23])[NH:19][C:18](=[O:24])[C:17]2([OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

参加物

7

反応物 4

HCID 807IodineHCID 113582-BromoanisoleHCID 5462224MagnesiumHCID 110093415,6-dichloro-1H-indole-2,3-dione

生成物 1

HCID 219255025,6-Dichloro-3-hydroxy-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one収率 80.6%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

7.5 g of 1-bromo-2-methoxybenzene are added dropwise to a suspension of 1.1 g of magnesium in 20 ml of ether containing a few crystals of iodine, the reflux being maintained once it has started. At the end of the addition, the mixture is heated at reflux for 2 hours. A suspension of 4.3 g of 5,6-dichloro-1H-indole-2,3-dione in 20 ml of THF is then added and the resulting mixture is refluxed for 30 minutes. After cooling to RT, the reaction mixture is poured into a water/ice/concentrated HCl mixture and extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is triturated in hot iso ether and the precipitate formed is filtered off by suction and washed with ether. 5.2 g of the expected product are obtained, m.p.=245–246° C.

後処理

  1. temperaturethe reflux being maintained once it
  2. additionAt the end of the addition
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 2 hours
  5. additionis then added
  6. temperaturethe resulting mixture is refluxed for 30 minutes
  7. extractionextracted with EtOAc
  8. dry with materialthe organic phase is dried over Na2SO4
  9. customthe solvent is evaporated off under vacuum
  10. customThe residue is triturated in hot iso ether
  11. customthe precipitate formed
  12. filtrationis filtered off by suction
  13. washwashed with ether

出典と根拠

ORDレコード
ord-565d91cc6fda462198d18bd8a8f68e27
出典データセット
uspto-grants-2006_10
特許番号
US07119086B2

関連ノート

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