2-Acetylpyridine → 2-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromide

HRID 1441141Notes

Reaction equation

HRID 1441141 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:5])[CH3:4]>C(Cl)(Cl)(Cl)Cl>[BrH:1].[Br:1][CH2:4][C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 142862-AcetylpyridineHCID 24408Bromine

Product 1

HCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture of bromine (4.28 ml) in 30 ml of carbon tetrachloride is added dropwise via addition funnel to a boiling mixture of 2-acetylpyridine (9.25 ml, Aldrich Chemical Co.) and carbon tetrachloride (65 ml). Addition is completed in 2 hr and within 15 minutes a solid began forming. Reflux continued for another 40 minutes before the reaction vessel is cooled to 0°. The solid precipitate is collected by filtration and dried (400°, 0.03 mm) for 3 hours to give the title compound, mp 212°-213°; NMR (CD3OD) 8.83-8.15, 3.86δ.

Workup

  1. additionAddition
  2. customa solid began forming
  3. temperatureReflux
  4. waitcontinued for another 40 minutes before the reaction vessel
  5. temperatureis cooled to 0°
  6. filtrationThe solid precipitate is collected by filtration
  7. customdried (400°, 0.03 mm) for 3 hours

Sources & evidence

ORD record
ord-bc71f857741e4ea79a433fe8910b444e
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

Loading…