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

HRID 735307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735307
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 688991572-{[6-(2,4-Difluorophenyl)-2-naphthyl]thio}benzonitrileAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f6438c4c933b4f62ab5370b0a7332d8c
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592456B2

Notizen zur Reaktion

Wird geladen…