Dimethylformamide → 3,5-Dibromo-4-pyridinecarboxaldehyde

HRID 1378379Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([Br:17])[C:15]=1[Li].CN([CH:21]=[O:22])C>>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([Br:17])[C:15]=1[CH:21]=[O:22]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 2724682Lithium diisopropylamide

HCID 178506638HCID 178506638, compound

Product 1

HCID 27629983,5-Dibromo-4-pyridinecarboxaldehyde

Procedure

Following the procedure of Gribble and Saulnier, (Tetrahedron Lett., 21:4137-4140 (1980)) reacting 3,5-bromopyridine (Aldrich) with LDA, and reacting the 3,5-dibromo-4-lithiopyridine with DMF provided 3,5-dibromo-4-pyridinecarboxaldehyde, which was then converted to the title compound by DIBAL reduction. 1H NMR (CDCl3) δ: 8.65 (s, 2H), 4.97 (s, 2H), 2.32 (s, br, 1H).

Sources & evidence

ORD record: ord-57e907affccd4c7088bf32ebe6efab63
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668141

Reaction notes

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