Iodo benzene diacetate → HCID 86746579, compound

HRID 1734332Notes

Reaction equation

HRID 1734332 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([Bi:13]([C:26]1[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:36][CH3:37])[CH:32]=3)[CH:27]=1)[C:14]1[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]=1)[CH:7]=[CH:6]2.[C:38]([OH:41])(=[O:40])[CH3:39].[C:42]([OH:45])(=[O:44])[CH3:43].IC1C=CC=CC=1>C(Cl)Cl>[C:38]([OH:41])(=[O:40])[CH3:39].[C:42]([OH:45])(=[O:44])[CH3:43].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([Bi:13]([C:26]1[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:36][CH3:37])[CH:32]=3)[CH:27]=1)[C:14]1[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]=1)[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 21469230HCID 21469230, compound

Product 1

HCID 86746579HCID 86746579, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tris(6-methoxynaphth-2-yl)bismuthine (100 mg, 0.158 mmol) in CH2Cl2 (8 mL) was added iodobenzene diacetate (200 mg, 0.621 mmol). The CH2Cl2 was removed in vacuo and the residue was dissolved in several milliliters of 4:1 hexanes/acetone plus small amount of CH2Cl2. The solution was passed through a silica gel plug and eluted with 4:1 hexanes/acetone. The filtrate was concentrated in vacuo. The residue was dissolved in 4:1 hexanes/acetone plus small amount of CH2Cl2 and passed through a second silica gel plug and eluted with 4:1 hexanes/acetone. The filtrate was concentrated in vacuo leaving 52 mg yellow residue that was used without further purification.

Workup

  1. customThe CH2Cl2 was removed in vacuo
  2. dissolutionthe residue was dissolved in several milliliters of 4:1 hexanes/acetone
  3. washeluted with 4:1 hexanes/acetone
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in 4:1 hexanes/acetone plus small amount of CH2Cl2
  6. washeluted with 4:1 hexanes/acetone
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f9424bc4387648758fef0b47a4c7845b
Source dataset
uspto-grants-1996_07
Patent number
US05532248

Reaction notes

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