Potassium Carbonate → 3-(2-Chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine

HRID 570811

Reaktionsgleichung

Reaktionsgleichung von HRID 570811
CS([O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1O>C(#N)C>[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 748142-Chloro-4-fluorophenolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Produkt 1

HCID 150422263-(2-Chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1-(diphenylmethyl)-3-azetidinyl methanesulfonate (363.8 g, 1.15 mol), potassium carbonate (330 g, 2.38 mol) and 2-chloro-4-fluorophenol (140 g, 0.96 mol) in acetonitrile (2.5 L) was heated under reflux for 4.5 hours. The cooled reaction mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate (1 L) and water (500 mL). The organic layer was separated, dried over sodium sulfate concentrated in vacuo and the residue was triturated with ethyl acetate/pentane/dichloromethane, 90:10:1, to afford the title compound as a white solid in quantitative yield, 350 g. 1H NMR (400 MHz, CDCl3) δ: 3.19 (m, 2H), 3.75 (m, 2H), 4.45 (m, 1H), 4.78 (m, 1H), 6.60 (m, 1H), 6.83 (m, 1H), 7.14 (m, 1H), 7.18-7.50 (m, 10H)

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4.5 hours
  3. customThe cooled reaction mixture
  4. concentrationwas then concentrated in vacuo
  5. customthe residue was partitioned between ethyl acetate (1 L) and water (500 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customthe residue was triturated with ethyl acetate/pentane/dichloromethane, 90:10:1

Quellen und Nachweise

ORD-Eintrag
ord-ff77a4901a444d52a9be963bbf0d647b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023872B2

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