Ethyl Acetate → 3-[(6-Amino-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrile

HRID 1874781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874781
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([O:18][C:19]2[C:24]([N+:25]([O-])=O)=[CH:23][CH:22]=[C:21]([CH3:28])[C:20]=2[F:29])[CH:17]=1)[C:13]#[N:14].CCOC(C)=O>O.C1COCC1>[NH2:25][C:24]1[C:19]([O:18][C:16]2[CH:15]=[C:12]([CH:11]=[C:10]([Cl:9])[CH:17]=2)[C:13]#[N:14])=[C:20]([F:29])[C:21]([CH3:28])=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 594515483-Chloro-5-[(2-fluoro-3-methyl-6-nitrophenyl)oxy]benzonitrile

Produkt 1

HCID 594516283-[(6-Amino-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrileAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydrosulfite (10.2 g, 58.7 mmol) dissolved in water (66 ml) was added dropwise to a vigorously stirred solution of 3-chloro-5-[(2-fluoro-3-methyl-6-nitrophenyl)oxy]benzonitrile (3.0 g, 9.78 mmol) dissolved in THF (33 mL). The reaction was stirred for 1 h then EtOAc (100 mL) was added and the layers were separated. The aqueous layer was extracted with EtOAc (2×50 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (2.5 g, 92%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.68 (d, 1H), 7.26 (dd, 1H), 7.16 (t, 1H), 6.85 (t, 1H), 6.51 (dd, 1H), 5.17 (d, 2H), 2.06 (d, 3H) MS: m/z 277.2 (M+1).

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f5a6a4869b90492a9c3e76cc19a60073
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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