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

HRID 1822962노트

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HRID 1822962 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23978Copper촉매HCID 7047Quinoline용매

반응 조건

온도
190 °C

실험 절차

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).

후처리

  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%

출처 및 근거

ORD 기록
ord-50cc5fb925d2488d8b72547a1b72d6db
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037932B2

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