Hydrochloric Acid → 7-fluoro-4-methoxy-1-benzothiophen-2(3H)-one

HRID 1822957노트

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HRID 1822957 반응식
[F:1][C:2]1[C:10]2[S:9][C:8](N(C)C)=[CH:7][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1.Cl.C1C[O:20]CC1>>[F:1][C:2]1[C:10]2[S:9][C:8](=[O:20])[CH2:7][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 22171134N-(7-fluoro-4-methoxy-1-benzothien-2-yl)-N,N-dimethylamine

생성물 1

HCID 235689637-fluoro-4-methoxy-1-benzothiophen-2(3H)-one수율 84%

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온도
80 °C

실험 절차

To a solution of N-(7-fluoro-4-methoxy-1-benzothien-2-yl)-N,N-dimethylamine (1.73 g, 7.7 mmol) in THF (25 mL) was added aqueous hydrochloric acid (1 N, 25 mL) and this was heated to 80° C. for 3 h. After cooling to room temperature then extracted with ether (100 mL), dried (MgSO4) and the solvent evaporated in vacuo to give a yellow solid. The residue was purified by flash chromatography in 5% ethyl acetate in hexane to give (1.3 g, 84%) of the title compound; δH (300 MHz, CHCl3) 6.97–6.87 (1H, m, ArH), 6.62–6.55 (1H, m, ArH), 3.91 (2H, s, CH2) and 3.85 (3H, s, OCH3).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthen extracted with ether (100 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated in vacuo
  5. customto give a yellow solid
  6. customThe residue was purified by flash chromatography in 5% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-95c9deb7ce7b4583bad325432a92dac9
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037932B2

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