Dimethylformamide → 4-Bromopyridine-3-carbaldehyde

HRID 1378378Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Li+].CC([N-]C(C)C)C.BrC1C=CN=CC=1[Li].CN([CH:28]=[O:29])C>>[Br:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH:28]=[O:29]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 881004-Bromopyridinium chloride

HCID 2724682Lithium diisopropylamide

HCID 178506760HCID 178506760, compound

Product 1

HCID 111167404-Bromopyridine-3-carbaldehyde

Procedure

Following the procedure of Gribble and Saulnier, Tetrahedron Lett., 21:4137-4140 (1980)) reacting 4-bromopyridine HCl (Aldrich) with 2 eq of LDA, and reacting the 4-bromo-3-lithiopyridine with DMF provided 4-bromo-3-pyridinecarboxaldehyde, which was converted to the title compound by DIBAL reduction. MS: 188 & 190 (M+H)+ ; 1H NMR (CDCl3) δ: 8.66 (s, 1H), 8.36 (d, J=6 Hz, 1H), 7.52 (d, J=6 Hz, 1H), 4.82 (d, J=6 Hz, 2H), 2.12 (t, J=6 Hz, 1H).

Sources & evidence

ORD record: ord-6afa86f54e3544919d10ad4b664a3c76
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668141

Reaction notes

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