Hydrogen Bromide → (6-Bromopyridin-3-yl)(4-fluorophenyl)methanone

HRID 648719Notes

Reaction equation

HRID 648719 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[BrH:17].[OH-].[Na+]>O>[Br:17][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 226266762-Chloro-5-(4-fluorobenzoyl)pyridine

Product 1

HCID 20145704(6-Bromopyridin-3-yl)(4-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.35 g 6-chloro-3-(4-fluorobenzoyl)-pyridine (see Ex. 5) and 50 ml 47% aqueous HBr are refluxed for 1 hr. After this time a control by gas chromatography reveals no starting chloro-derivative is present. The reaction liquid is added to water, and a yellow solid is formed. The mixture is basified with concentrated NaOH, and the crystalline solid is filtered and recrystallised from methanol:water. Yield: 0.9 g title product, as white crystals, m.p. 97°-8° C.; UV (water): λmax. 278 nm, ε: 16,600; Br 28.34 (28.53); F 7.11 (6.78).

Workup

  1. customThe reaction liquid
  2. customa yellow solid is formed
  3. filtrationthe crystalline solid is filtered
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-96a519712faf4e24bd8d68b7901be974
Source dataset
uspto-grants-1988_04
Patent number
US04736037

Reaction notes

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