Iodo benzene diacetate → HCID 86746579, compound

HRID 257688Notes

Reaction equation

HRID 257688 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 tri(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-b87c81172bcf4256943a4de12a7af3b4
Source dataset
uspto-grants-1993_11
Patent number
US05262533

Reaction notes

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