Dichloromethane → HCID 15337393, compound

HRID 2269569Notes

Reaction equation

HRID 2269569 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[S:14][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(Cl)Cl.[Br:23]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:23][C:15]1[S:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 18347213HCID 18347213, compound

Product 1

HCID 15337393HCID 15337393, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(4-(methanesulfonyl)phenyl)benzo[b]-thiophene (1 g) from Step 2 in CH2Cl2 (70 mL) one equivalent of a 1M Br2 solution in CCl4 was added. The mixture was stirred at 25° C. for 2 hrs, then a 10% Na2S2O3 solution was added. After extraction with EtOAc, the organic layers were washed with a saturated solution of NaHCO3 (3×), brine, and dried over MgSO4, filtered and the solvent evaporated under vacuum. Purification by column chromatography using 5% EtOAc in toluene afforded the title compound.

Workup

  1. extractionAfter extraction with EtOAc
  2. washthe organic layers were washed with a saturated solution of NaHCO3 (3×), brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated under vacuum
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-fd19ead76edf4a46b06d97ef878f15fc
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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