2,5-Dibromopyridine → 5-Bromo-2-(4-octylphenyl)pyridine

HRID 1857299Notes

Reaction equation

HRID 1857299 reaction equation
[Mg].[CH2:2]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=1>O1CCCC1>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[CH:14]=[CH:15][C:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:11][CH:12]=2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 693532,5-DibromopyridineHCID 142854p-BromophenyloctaneHCID 5462224Magnesium

Product 1

HCID 184718205-Bromo-2-(4-octylphenyl)pyridineYield 108.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A Grignard reagent was prepared from magnesium (2.3 g) and 4-octyl-1-bromobenzene (25 g) dissolved in dry tetrahydrofuran (hereinafter abbreviated to THF, 200 ml). To this Grignard reagent were added 2,5-dibromopyridine (23 g) and tetrakistriphenylphosphin paradiun (0) complex (hereinafter abbreviated to Pd(TPP)4, 0.57 g). The reaction mixture was heated to keep refluxing for about 2 hours. After cooling the mixture, organic matter was extracted from the mixture with ether, followed by sequential washing the extract with aqueous ammonium chloride and distilled water to separate an organic layer which was dried over MgSO4. Filtering off the desiccant and distilling off the solvent from the organic layer, the layer gave a residue which was purified by silica gel column chromatography to give 5-bromo-2-(4-octylphenyl)pyridine (35 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto keep refluxing for about 2 hours
  3. temperatureAfter cooling the mixture, organic matter
  4. extractionwas extracted from the mixture with ether
  5. washby sequential washing the
  6. extractionextract with aqueous ammonium chloride
  7. distillationdistilled water
  8. customto separate an organic layer which
  9. dry with materialwas dried over MgSO4
  10. filtrationFiltering off the desiccant and
  11. distillationdistilling off the solvent from the organic layer
  12. customthe layer gave a residue which
  13. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0cbc0f83abeb464a9db87681551f8f0e
Source dataset
uspto-grants-2000_11
Patent number
US06146547

Reaction notes

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