Sodium Bicarbonate → 5-Bromo-1,3-dihydro-benzo(c)thiophene 2,2-dioxide

HRID 748889Notes

Reaction equation

HRID 748889 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6]S[CH2:8][C:4]=2[CH:3]=1.O[O:12][S:13]([O-:15])=O.[K+].S(=O)(O)[O-].[Na+].C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][S:13](=[O:15])(=[O:12])[CH2:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfiteHCID 598014895-Bromo-1,3-dihydro-2-benzothiophene

Product 1

HCID 2883965-Bromo-1,3-dihydro-benzo(c)thiophene 2,2-dioxideYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 5-bromo-1,3-dihydro-benzo[c]thiophene (1.25 g, 5.79 mmol) in methanol (25 mL) and add oxone (10.7 g, 17.4 mmol). Stir the reaction mixture for 2 hours at 0° C. and then add a 1M aqueous sodium bisulfite solution (100 mL). Stir the reaction mixture for 10 minutes and add saturated NaHCO3 solution (200 mL). Extract the aqueous layer with CH2Cl2 (3×1 00 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 0-5% MeOH/CH2Cl2) to give 930 mg of 5-bromo-1,3-dihydro-benzo[c]thiophene 2,2-dioxide (65%).

Workup

  1. stirringStir the reaction mixture for 10 minutes
  2. extractionExtract the aqueous layer with CH2Cl2 (3×1 00 mL)
  3. dry with materialCombine the organic layers and dry with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify by flash column chromatography (silica gel, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e2639faad0e841648df3139585c9550b
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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