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

HRID 732754

反応式

HRID 732754 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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 (3×100 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%).

後処理

  1. stirringStir the reaction mixture for 10 minutes
  2. extractionExtract the aqueous layer with CH2Cl2 (3×100 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)

出典と根拠

ORDレコード
ord-7c085e5eaa9c4274a1e99e22f1d16ac9
出典データセット
uspto-grants-2009_09
特許番号
US07585977B2

関連ノート

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