Trimethylsilyl cyanide → 4-Bromo-2-cyanopyridine

HRID 1289477

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N+:5]([O-])=[CH:4][CH:3]=1.C[Si]([C:13]#[N:14])(C)C>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:13]#[N:14])[CH:3]=1

Participants

Reactant 2

HCID 82115Trimethylsilyl cyanide

HCID 1397084-Bromopyridin-1-ium-1-olate

Product 1

HCID 6932834-Bromo-2-cyanopyridine

Procedure

The title compound was prepared from 4-bromopyridine-1-oxide (Rec. Trav. chim., 1951, 70, 581) and trimethylsilyl cyanide, using the procedure described in Chem. Pharm. Bull., 1985, 33, 565, and obtained as a solid (49% yield), m.p. 88°-93° C. Rf 0.53 (SS 11). Found: C,39.15; H,1.50; N,15.07. C6H3BrN2 requires C,39.37; E,1.65; N,15.30%.

Sources & evidence

ORD record: ord-b9e28d64c47c4e2bbcdbe54b64ba0176
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750520

Linked notes

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