Hydrogen Bromide → 2-(5-Bromo-2-fluorophenyl)-3-fluoropyridine

HRID 586287Notes

Reaction equation

HRID 586287 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=1.N([O-])=O.[Na+].C(Cl)Cl.[BrH:23]>[Cu]Br>[Br:23][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 223295254-Fluoro-3-(3-fluoropyridin-2-yl)phenylamineHCID 23668193Sodium Nitrite

Product 1

HCID 115435872-(5-Bromo-2-fluorophenyl)-3-fluoropyridine

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Procedure

4-Fluoro-3-(3-fluoropyridin-2-yl)phenylamine was subjected to reaction with sodium nitrite, in hydrobromic acid in the presence of copper(I) bromide, according to the method of Example 23. 2-(5-Bromo-2-fluorophenyl)-3-fluoropyridine was obtained by chromatography (silica gel, CH2Cl2) as a pink solid: MS (ES+) m/z 270, 272 [M+H]+.

Sources & evidence

ORD record
ord-112c0d8dadbb4192b8dcb1c07ebd98c2
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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