4-Bromopyridinium chloride → 4-(4-Pyridyl)benzaldehyde

HRID 1266034Notes

Reaction equation

HRID 1266034 reaction equation
N1C=C[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.Cl.BrC1C=C[N:20]=[CH:19][CH:18]=1>C(N(CC)CC)C>[N:20]1[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:18][CH:19]=1

Participants

4

Reactant 2

HCID 881004-Bromopyridinium chlorideHCID 15152404-Pyridin-2-ylbenzaldehyde

Product 1

HCID 6396734-(4-Pyridyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This aldehyde was prepared using the procedure for 4-pyridin-2-yl-benzaldehyde in Example 126 from 4-bromopyridine hydrochloride, triethylamine and 4-formylboronic acid to give a yellow crystalline solid (51%): mp=90-91° C.; Rf=0.08 (30% EtOAc/hexanes); IR (KBr) 1697, 1595, 1214, 1169, 801 cm−1; 1H NMR (CDCl3) δ 7.74 (d, 2H, J=5.8 Hz), 7.84 (d, 2H, J=8.3 Hz), 8.05 (d, 2H, J=8.1 Hz), 8.77-8.78 (m, 2H), 10.11 (s, 1H). LRMS 184 (M+H).

Sources & evidence

ORD record
ord-0a619bc0c1f1432798810bbe175af5c5
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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