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

HRID 2220303ノート

反応式

HRID 2220303 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d2f28074afb84230a5da1b3cb61bad21
出典データセット
uspto-grants-2008_08
特許番号
US07417064B2

反応ノート

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