Dimethylformamide → 4-Bromopyridine-3-carbaldehyde

Participants

Reaction Steps

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).

Provenance & Evidence