Ethyl Acetate → (2,4-Dichloro-phenyl)-(6-hydroxy-3-trifluoromethyl-benzofuran-2-yl)-methanone

HRID 29244

반응식

HRID 29244 반응식
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[C:10]([F:13])([F:12])[F:11].Cl[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])=[O:18].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:17]([C:16]1[O:1][C:2]2[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=2[C:9]=1[C:10]([F:13])([F:12])[F:11])=[O:18]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 202502,2',4'-TrichloroacetophenoneHCID 142973321-(2,4-Dihydroxyphenyl)-2,2,2-trifluoroethanone

생성물 1

HCID 59788864(2,4-Dichloro-phenyl)-(6-hydroxy-3-trifluoromethyl-benzofuran-2-yl)-methanone수율 33.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 1-(2,4-dihydroxy-phenyl)-2,2,2-trifluoro-ethanone (1.00 g, 4.85 mmol) and 2-chloro-1-(2,4-dichlorophenyl)ethanone (1.08 g, 4.85 mmol, 1.0 eq) in anhydrous N,N-dimethylformamide (10 mL) was added potassium carbonate (1.01 g, 7.28 mmol, 1.5 eq). The reaction mixture was stirred at 90° C. for 16 h. The mixture was cooled to room temperature and then poured into ethyl acetate (100 mL) and water (100 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (2×100 mL), dried over Na2SO4, filtrated, and evaporated in vacuo. The residue was purified by column chromatography eluted with 5% EtOAc/hexane then 30% EtOAc/hexane solution to afford a yellow solid (610 mg, 33.5%) as product. 1H-NMR (CDCl3): δ 7.76 (d, J=8.7 Hz, 1H), 7.52 (d, J=8.5 Hz, 1H), 7.50 (d, J=1.7 Hz, 1H), 7.41 (dd, J=8.1, 1.9 Hz, 1H), 7.01 to 6.95 (m, 2H), 5.49 (s, 1H); LC-MS (MH+=375/377).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed with water (2×100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with 5% EtOAc/hexane

출처 및 근거

ORD 기록
ord-769aacdff93b444b98b43d337bf271a0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420066B2

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