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

HRID 31353

Reaction equation

HRID 31353 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 219255025,6-Dichloro-3-hydroxy-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-oneYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.57 g of 1-bromo-2-methoxybenzene are added dropwise to a suspension of 0.72 g of magnesium in 15 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 refluxed for 2 hours. A suspension of 2.7 g of 5,6-dichloro-1H-indole-2,3-dione in 30 ml of THF is then added and the 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 slurried in hot iso ether and the precipitate formed is spin-filtered off and washed with ether. 3 g of the expected product are obtained.

Workup

  1. temperaturethe reflux being maintained once it
  2. additionAt the end of the addition
  3. temperaturethe mixture is refluxed for 2 hours
  4. additionis then added
  5. temperaturethe mixture is refluxed for 30 minutes
  6. extractionextracted with EtOAc
  7. dry with materialthe organic phase is dried over Na2SO4
  8. customthe solvent is evaporated off under vacuum
  9. customthe precipitate formed
  10. filtrationis spin-filtered off
  11. washwashed with ether

Sources & evidence

ORD record
ord-8a70d1b019c341bfa8531040820b3ea8
Source dataset
uspto-grants-2008_09
Patent number
US07425566B2

Linked notes

Loading…