Bromine → 2-Bromo-6-phenylpyridine

HRID 1513622Notes

Reaction equation

HRID 1513622 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.[Br:14]Br.N([O-])=O.[Na+]>Br>[Br:14][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 5984302-Amino-6-phenylpyridineHCID 23668193Sodium Nitrite

Product 1

HCID 5686792-Bromo-6-phenylpyridineYield 80.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
-20 °C

Procedure

48% HBr 50 mL was added to 6.9 g (40 mmol) of 2-amino-6-phenylpyridine and stirred. The solution was cooled down to −20° C., and 7.7 g (48 mmol) of bromine was dropwise added thereto. Further, 2.8 g (40 mmol) of sodium nitrite was dropwise added thereto. The solution was stirred for 3 hours while elevating the temperature up to room temperature. After finishing the reaction, the solution was extracted with ethyl acetate, and the aqueous layer was removed. The organic layer was dried on anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was refined by silica gel chromatography to obtain 7.5 g (yield: 80%) of 2-bromo-6-phenylpyridine.

Workup

  1. stirringThe solution was stirred for 3 hours
  2. customup to room temperature
  3. customthe reaction
  4. extractionthe solution was extracted with ethyl acetate
  5. customthe aqueous layer was removed
  6. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-16ec8074d8864bcc824b8aa06e3b3b70
Source dataset
uspto-grants-2012_07
Patent number
US08217570B2

Reaction notes

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