Sodium Cyanide → 1-(3-Bromo-4-fluorophenyl)-1-cyanomethanol

HRID 272657

Reaktionsgleichung

Reaktionsgleichung von HRID 272657
S(=O)(O)[O-].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[F:15])[CH:10]=[O:11].[C-:16]#[N:17].[Na+]>O.CCOCC>[Br:6][C:7]1[CH:8]=[C:9]([CH:10]([C:16]#[N:17])[OH:11])[CH:12]=[CH:13][C:14]=1[F:15]

Komponenten

6

Edukt 3

HCID 8929Sodium CyanideHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 23665763Sodium Bisulfite

Produkt 1

HCID 434366161-(3-Bromo-4-fluorophenyl)-1-cyanomethanolAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of sodium bisulfite (28.3 g, 271 mmol) in water at 50° C. is treated with 3-bromo-4-fluorobenzaldehyde (45.8 g, 225 mmol), stirred at 50° C. for 2 h, cooled with an ice bath, diluted with ether, treated dropwise with an aqueous solution of sodium cyanide (12.2 g, 248 mmol) over a period of 30 min and stirred at room temperature overnight. The reaction mixture is separated, and the aqueous phase is extracted with ether. The extracts are combined with the organic phase, washed with brine, dried over magnesium sulfate and concentrated to dryness to afford the title compound as a clear oil, 47.6 g (92% yield), identified by NMR analysis. 1H NMR (300 MHz, CDCl3) δ 7.75 (m, 1H), 7.47 (m, 1H), 7.23 (m, 1H), 5.54 (m, 1H), 3.19 (m, 1H).

Aufarbeitung

  1. temperaturecooled with an ice bath
  2. stirringstirred at room temperature overnight
  3. customThe reaction mixture is separated
  4. extractionthe aqueous phase is extracted with ether
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6d1b69fd37f049abab1d5c9a36b457bc
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456186B2

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