Chlorosuccinimide → HCID 15158732, compound

HRID 1084420Notes

Reaction equation

HRID 1084420 reaction equation
O1CCCC1.C([N-]C(C)C)(C)C.[Li+].[Br: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][CH:16]=1.[Li+].BrC1C=CC2C=C(S([O-])=O)OC=2C=1.[Li+].[Cl:42]N1C(=O)CCC1=O>CCOCC.C1CCCCC1.ClCCl>[Br:14][C:15]1[C:23]2[CH:22]=[C:21]([S:24]([Cl:42])(=[O:26])=[O:25])[O:20][C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 23672793HCID 23672793, compoundHCID 23694644HCID 23694644, compound

Product 1

HCID 15158732HCID 15158732, 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 (430 ml) was added dropwise 1.5 M lithium diisopropylamide mono(tetrahydrofuran) in cyclohexane (430 ml) under nitrogen atmosphere at -70° C. After stirring for 30 minutes, into the solution was bubbled sulfur dioxide for 1 hour with stirring at -60° C. Then the solution was stirred for 3 hours at room temperature and the formed precipitate was separated by filtration to give a mixture of lithium 4-bromobenzo[b]furan-2-sulfinate and lithium 6-bromobenzo[b]furan-2-sulfinate. To the suspension of the products in dichloromethane (2 1) was added N-chlorosuccinimide (96 g) at -50° C. and stirred for 3 hours under ice-cooling. Insoluble matters were filtered off and dichloromethane was removed in vacuo and the residue was purified by silica gel column chromatography to give 14.1 g of the objective compound.

Workup

  1. customwas bubbled sulfur dioxide for 1 hour
  2. stirringwith stirring at -60° C
  3. stirringThen the solution was stirred for 3 hours at room temperature
  4. customthe formed precipitate was separated by filtration
  5. customto give
  6. stirringstirred for 3 hours under ice-
  7. temperaturecooling
  8. filtrationInsoluble matters were filtered off
  9. customdichloromethane was removed in vacuo
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fdd6d00775104e9994397231ca007a55
Source dataset
uspto-grants-1991_04
Patent number
US05004751

Reaction notes

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