Sodium methanethiolate → 6-Methylsulfanylbenzo[b]thiophene

HRID 1986208노트

반응식

HRID 1986208 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 198037266-Methylsulfanylbenzo[b]thiophene수율 83.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83d3ffda27a649bfb8c37423a07d4f9b
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547691B2

반응 노트

불러오는 중…