Cyanide → 3-Bromopyridine-2-carbonitrile

HRID 423177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423177
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.[C-:9]#[N:10]>N1C=CC=CC=1>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 5975CyanideHCID 142763Pyridine, 3-bromo-, 1-oxide

Produkt 1

HCID 8176943-Bromopyridine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

In Scheme I is described the preparation of pyridine intermediates (5) and (6). In Scheme I, Step 1,3-bromopyridine (1) is oxidized to 3-bromo-pyridine-N-oxide (2). In Scheme I, Step 2, cyanide addition gives 3-bromo-pyridine-2-carbonitrile (3). The nitrile of formula (3) is hydrolyzed to the carboxylic acid and esterified with acid catalysis to the ester of formula (4). In Scheme I, Step 4, the ester is reduced to the pyridylmethanol of formula (5a) using sodium borohydride.

Quellen und Nachweise

ORD-Eintrag
ord-0d6d80b5e8f347ff8cbffc974dbc79d0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101761B2

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