Nitromethane → (E)-1-Chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzene

HRID 920290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920290
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].C([O-])(=O)C.[NH4+].[N+:26]([CH3:29])([O-:28])=[O:27]>CC(O)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10](/[CH:11]=[CH:29]/[N+:26]([O-:28])=[O:27])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 866661874-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde

Produkt 1

HCID 67775160(E)-1-Chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzeneAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 4-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde (13 g, 43.2 mmol) and ammonium acetate (1.67 g, 21.62 mmol) in HOAc (40 mL), was added nitromethane (6.99 mL, 130 mmol). The reaction mixture was stirred at 120° C. for 5 h, and concentrated. The residue was dissolved in DCM (150 mL), washed with sat. aqueous NaHCO3 (100 mL×2), brine and then, dried over anhydrous Na2SO4 and concentrated to afford the title compound as a brown solid (14.3 g, 63% yield).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM (150 mL)
  3. washwashed with sat. aqueous NaHCO3 (100 mL×2), brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b097404ac136458f9bc43d512de4ac33
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273054B2

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