4-Chloropyridine → 4-Chloro-2-(3-bromophenyl)-pyridine

HRID 973550Notes

Reaction equation

HRID 973550 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Li])[CH:5]=[CH:6][CH:7]=1.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.C1(OC(Cl)=O)C=CC=CC=1.[N].N1C=CC=CC=1>>[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH:11]=1

Participants

5

Reactant 4

HCID 122884-ChloropyridineHCID 15891Phenyl chloroformateHCID 178506674HCID 178506674, compoundHCID 178507885HCID 178507885, compound

Product 1

HCID 199886504-Chloro-2-(3-bromophenyl)-pyridine

Procedure

Starting from 3-bromophenyllithium, 4-chloropyridine and chloroformic acid phenyl ester (for the acylation of the pyridine nitrogen), the title compound is prepared analogously to J. Org. Chem. 50, 4410 (1985). A corresponding 1-acyl-1,2-dihydropyridine is formed as intermediate and is aromatised by reaction with o-chloroanil (=3,4,5,6-tetrachloro-1,2-benzoquinone) to form the title compound.

Sources & evidence

ORD record
ord-90d99d4c422947d3b0e5dabb1c6dab44
Source dataset
uspto-grants-1991_11
Patent number
US05064832

Reaction notes

Loading…