Hydrochloric Acid → Ethyl 2-(3-Bromo-4-fluorophenyl)-2-hydroxyethanimidoate Hydrochloride

HRID 272658

Reaktionsgleichung

Reaktionsgleichung von HRID 272658
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([C:11]#[N:12])[OH:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:13]([OH:15])[CH3:14].[ClH:16]>CCOCC>[ClH:16].[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:10])[C:11](=[NH:12])[O:15][CH2:13][CH3:14])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 434366161-(3-Bromo-4-fluorophenyl)-1-cyanomethanol

Produkt 1

HCID 68899226Ethyl 2-(3-Bromo-4-fluorophenyl)-2-hydroxyethanimidoate HydrochlorideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 1-(3-bromo-4-fluorophenyl)-1-cyanomethanol (47.5 g, 206 mmol) and ethanol (10.9 g, 237 mmol) in ether is cooled with an ice bath and treated dropwise with HCl (258 mL of a 1.0 M solution in diethyl ether, 258 mmol) over a period of 40 min., stirred at ice-bath temperature for 2 h, stored at 0° C. for 6 days, warmed to room temperature, diluted with hexanes and filtered. The filtercake is dried to afford the title compound as a white solid, 39.8 g (62% yield), identified by NMR and mass spectral analyses. The title compound is a mixture of E and Z isomers. 1H NMR (300 MHz, CD3OD) δ 7.78 (m, 1H), 7.49 (m, 1H), 7.28 (m, 1H), 5.54 and 5.17 (2m, 1H), 4.45 and 4.15 (2m, 2H), 1.38 and 1.20 (2t, 3H); ESI MS m/z 261 [C10H11BrFNO2+H]+

Aufarbeitung

  1. waitstored at 0° C. for 6 days
  2. filtrationfiltered
  3. customThe filtercake is dried

Quellen und Nachweise

ORD-Eintrag
ord-8b70e695835e4a4793d12951be66261e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456186B2

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