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

HRID 1243317

반응식

HRID 1243317 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-565d91cc6fda462198d18bd8a8f68e27
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119086B2

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