3-Bromopyridine → 4-(Pyridin-3-yl)benzaldehyde

HRID 1266033Notes

Reaction equation

HRID 1266033 reaction equation
N1C=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.BrC1[CH:17]=[N:18]C=CC=1>>[N:18]1[CH:5]=[CH:4][CH:3]=[C:2]([C:7]2[CH:8]=[CH:9][C:10]([CH:11]=[O:12])=[CH:13][CH:14]=2)[CH:17]=1

Participants

3

Reactant 2

HCID 122863-BromopyridineHCID 15152404-Pyridin-2-ylbenzaldehyde

Product 1

HCID 36930464-(Pyridin-3-yl)benzaldehyde

Procedure

This aldehyde was prepared using the procedure for 4-pyridin-2-yl-benzaldehyde in Example 126 from 3-bromopyridine and 4-formylboronic acid to give a white crystalline solid (94%): mp=53-55° C.; Rf=0.08 (30% EtOAc/hexanes); IR (KBr) 1700, 1605, 1219 cm−1; 1H NMR (CDCl3) δ 7.55-7.60 (m, 1H), 7.76-7.79 (m, 2H), 8.01-8.05 (m, 2H), 8.08-8.12 (m, 1H), 8.69-8.71 (m, 1H), 8.94-8.95 (m, 1H), 10.10 (s, 1H). LRMS 184 (M+H).

Sources & evidence

ORD record
ord-8d13532ad9e744328f38d73d47a8f099
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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