Hydrochloric Acid → Benzo[b]thiophene, 7-fluoro-4-methoxy-

HRID 1822962ノート

反応式

HRID 1822962 の反応式
[F:1][C:2]1[C:10]2[S:9][C:8](C(O)=O)=[CH:7][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[F:1][C:2]1[C:10]2[S:9][CH:8]=[CH:7][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23568964476199-03-8

生成物 1

HCID 22171140Benzo[b]thiophene, 7-fluoro-4-methoxy-

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 7047Quinoline溶媒

反応条件

温度
190 °C

実験手順

A mixture of 7-fluoro-4-methoxy-1-benzothiophene-2-carboxylic acid (61.4 g, 271 mmol) and copper powder (22.4 g, 352 mmol) in quinoline (500 mL) was heated at 190° C. for 1 h. Cooled to ambient and poured onto aqueous hydrochloric acid (2 N, 750 mL). Stirred with ethyl acetate (500 mL) for 15 minutes. Filtered through Celite, washing with ethyl acetate. The aqueous layer was extracted into ethyl acetate and the combined organic layers were washed with aqueous hydrochloric acid (2 N, 500 mL), water (500 mL), brine (500 mL), dried over MgSO4 and evaporated in vacuo. Purified by column chromatography, eluting silica gel with iso-hexane/diethyl ether 0–5% to give the product as a brown oil which crystallised to give the title compound (41.3 g, 84%); δH (300 MHz, CDCl3) 7.51 (1H, m, ArH), 7.38 (1H, d, ArH), 6.98 (1H, t, ArH), 6.65 (1H, dd, ArH) and 3.92 (3H, s, OCH3).

後処理

  1. temperatureCooled
  2. filtrationFiltered through Celite
  3. washwashing with ethyl acetate
  4. extractionThe aqueous layer was extracted into ethyl acetate
  5. washthe combined organic layers were washed with aqueous hydrochloric acid (2 N, 500 mL), water (500 mL), brine (500 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customPurified by column chromatography
  9. washeluting silica gel with iso-hexane/diethyl ether 0–5%

出典と根拠

ORDレコード
ord-50cc5fb925d2488d8b72547a1b72d6db
出典データセット
uspto-grants-2006_05
特許番号
US07037932B2

反応ノート

読み込み中…