Ethylene Glycol → 2-{[6-(2,4-Difluorophenyl)-2-naphthyl]thio}benzonitrile

HRID 735307노트

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HRID 735307 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([SH:19])[CH:13]=[CH:12]2.I[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24].C(=O)([O-])[O-].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([S:19][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24])[CH:13]=[CH:12]2

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 27593582-IodobenzonitrileHCID 689014886-(2,4-Difluorophenyl)-2-naphthyl hydrosulfide

생성물 1

HCID 688991572-{[6-(2,4-Difluorophenyl)-2-naphthyl]thio}benzonitrile수율 20.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

6-(2,4-Difluorophenyl)-2-naphthyl hydrosulfide (Step 2, 0.78 g) was dissolved in isopropyl alcohol (15 mL). 2-Iodobenzonitrile (0.66 g, 2.88 mmol), copper(I) iodide (29 mg, 0.15 mmol), potassium carbonate (0.8 g, 5.79 mmol) and ethylene glycol (320 μL) were added and the reaction heated to 80° C. under nitrogen overnight. Ethyl acetate was added to the cooled reaction mixture and stirred for 15 minutes. The mixture was filtered and the filtrate evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 10-20% ethyl acetate/isohexane, followed by recrystallisation from ethyl acetate/isohexane, to give 2-{[6-(2,4-difluorophenyl)-2-naphthyl]thio}benzonitrile (216 mg, 20%). 1H NMR (500 MHz, CDCl3) δ 8.04 (1H, s), 7.97 (1H, s), 7.88 (2H, t, J=7.8 Hz), 7.68 (2H, d, J=8.0 Hz), 7.54-7.48 (2H, m), 7.43-7.39 (1H, m), 7.28 (1H, t, J=7.6 Hz), 7.19 (1H, d, J=7.9 Hz), 7.03-6.95 (2H, m).

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was purified by flash column chromatography on silica
  4. washeluting with 10-20% ethyl acetate/isohexane
  5. customfollowed by recrystallisation from ethyl acetate/isohexane

출처 및 근거

ORD 기록
ord-f6438c4c933b4f62ab5370b0a7332d8c
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592456B2

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