HCID 21584088, 화합물 → HCID 21584080, 화합물

HRID 617726노트

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HRID 617726 반응식
[C:1]1([S:7][C:8]2([O:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=3[N+:23]([O-])=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O.C(O)(=O)C.[Fe]>[C:1]1([S:7][C:8]2([O:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:20])([F:21])[F:22])=[CH:14][C:13]=3[NH2:23])[CH2:9][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 1

HCID 21584088HCID 21584088, 화합물

생성물 1

HCID 21584080HCID 21584080, 화합물수율 78%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

Iron powder (13.5 g, 241 mmol) was added to a suspension of 2-(1-phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)nitrobenzene (Description 4, 11.27 g, 30,1 mmol) in water (300 mL) and acetic acid (75 mL) and the mixture was stirred at 80° C. overnight. The mixture was cooled and filtered through celite, washing with ether. The filtrate was extracted with ether, the combined organic fractions were washed with aqueous sodium hydroxide (1M), dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (90:10 increasing to 80:20), to give the title compound as a yellow solid (8 g, 78%). 1H NMR (360 MHz, CDCl3) δ 7.48 (2H, m), 7.34-7.23 (3H, m), 7.15 (1H, d, J 8.74 Hz), 6.60-6.56 (2H, m), 3.78 (2H, br s), 1.49-1.46 (2H, m), and 1.39-1.35 (2H, m).

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washwashing with ether
  4. extractionThe filtrate was extracted with ether
  5. washthe combined organic fractions were washed with aqueous sodium hydroxide (1M)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with hexane/Et2O (90:10 increasing to 80:20)

출처 및 근거

ORD 기록
ord-4a960977485440eea8e386228acad22f
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952315

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