Iodine → HCID 23031211, compound

HRID 1766658Notes

Reaction equation

HRID 1766658 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:29]I>ClCCl.C([O-])(=O)C.[Ag+]>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[CH:11][C:10]=1[I:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 807IodineHCID 23031249HCID 23031249, compound

Product 1

HCID 23031211HCID 23031211, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-benzyloxyphenoxy)-5-methyl-7-nitroindane (3.21 g) in dichloromethane (15 mL) was added silver acetate (1.86 g). After adding iodine (2.60 g), the mixture was stirred under an argon atmosphere in the dark at room temperature for 2 days. The insoluble material was removed by filtration. The filtrate was washed with an aqueous solution of sodium sulfite (1.7 g/40 mL), a saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (4.18 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. washThe filtrate was washed with an aqueous solution of sodium sulfite (1.7 g/40 mL)
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9daf015bba444d70be112203d2f00890
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

Loading…