Chlorosuccinimide → HCID 15158734, compound

HRID 2253687Notes

Reaction equation

HRID 2253687 reaction equation
O1CCCC1.C([N-]C(C)C)(C)C.[Li+].[Cl:14][C:15]1[C:23]2[CH:22]=[C:21]([S:24]([O-:26])=[O:25])[O:20][C:19]=2[CH:18]=[CH:17][C:16]=1[Cl:27].[Li+].[Cl:29][C:30]1[C:41]([Cl:42])=[CH:40][C:33]2[O:34][C:35]([S:37]([O-:39])=[O:38])=[CH:36][C:32]=2[CH:31]=1.[Li+].[Cl:44]N1C(=O)CCC1=O>CCOCC.C1CCCCC1.ClCCl>[Cl:14][C:15]1[C:23]2[CH:22]=[C:21]([S:24]([Cl:29])(=[O:26])=[O:25])[O:20][C:19]=2[CH:18]=[CH:17][C:16]=1[Cl:27].[Cl:29][C:30]1[C:41]([Cl:42])=[CH:40][C:33]2[O:34][C:35]([S:37]([Cl:44])(=[O:39])=[O:38])=[CH:36][C:32]=2[CH:31]=1

Participants

9

Reactant 4

HCID 31398ChlorosuccinimideHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 23694643HCID 23694643, compoundHCID 23694646HCID 23694646, compound

Product 2

HCID 15158734HCID 15158734, compoundHCID 15158735HCID 15158735, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of the mixture obtained in Step 2 (100 g) in anhydrous ether (440 ml) was added dropwise 1.5 M lithium diisopropylamide mono(tetrahydrofuran) in cyclohexane (440 ml) under nitrogen atmosphere at -70° C. over 1 hour, then into the solution was bubbled sulfur dioxide for 1.5 hours at -70° C. After stirring for 1 hour at room temperature, the solvent was removed in vacuo and ether was added to the residue. The formed precipitate was separated by filtration to give a mixture of lithium 4,5-dichlorobenzo[b]furan-2-sulfinate and lithium 5,6-dichlorobenzo[b]furan-2-sulfinate. To the suspension of the products in dichloromethane (1.8 l) was added N-chlorosuccinimide (92.1 g) at -50° C. and stirred for 1.5 hours. At room temperature, insoluble matters were filtered off and dichloromethane was removed in vacuo and the residue was purified by silica gel column chromatography to give 17.4 g of 4,5-dichlorobenzo[b]furan-2-ylsulfonyl chloride and 7.4 g of 5,6-dichlorobenzo[b]furan-2-ylsulfonyl chloride, respectively.

Workup

  1. custominto the solution was bubbled sulfur dioxide for 1.5 hours at -70° C
  2. customthe solvent was removed in vacuo and ether
  3. additionwas added to the residue
  4. customThe formed precipitate was separated by filtration
  5. customto give
  6. stirringstirred for 1.5 hours
  7. filtrationAt room temperature, insoluble matters were filtered off
  8. customdichloromethane was removed in vacuo
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5d3a2927577e422c9ea99daa8275c10d
Source dataset
uspto-grants-1993_08
Patent number
US05232936

Reaction notes

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