Sodium methanethiolate → 6-Methylsulfanylbenzo[b]thiophene

HRID 1986208ノート

反応式

HRID 1986208 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[CH3:11][S-:12].[Na+]>CN(C=O)C>[CH3:11][S:12][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1

参加物

4

反応物 2

HCID 4378561Sodium methanethiolateHCID 127444006-Bromo-benzo[b]thiophene

生成物 1

HCID 198037266-Methylsulfanylbenzo[b]thiophene収率 83.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 6-bromobenzo[b]thiophene (2.0 g, 9.4 mmol) and sodium thiomethoxide (1.30 g, 18.8 mmol) in DMF (15 mL) is stirred at 90° C. under nitrogen for 6 hours. The reaction is cooled to room temperature, extracted with ethyl acetate and saturated aqueous sodium chloride, washed with 2 N aqueous NaOH solution, saturated aqueous sodium chloride, dried over Na2SO4, filtered, and evaporated. The residue is purified by chromatography on silica gel, eluting with ethyl acetate:hexanes 3:7, to give the title product as a red liquid (1.41 g) which is used for next reaction without further purification.

後処理

  1. temperatureThe reaction is cooled to room temperature
  2. extractionextracted with ethyl acetate and saturated aqueous sodium chloride
  3. washwashed with 2 N aqueous NaOH solution, saturated aqueous sodium chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on silica gel
  8. washeluting with ethyl acetate:hexanes 3:7

出典と根拠

ORDレコード
ord-83d3ffda27a649bfb8c37423a07d4f9b
出典データセット
uspto-grants-2009_06
特許番号
US07547691B2

反応ノート

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