Chloride → 2-(2,4-dimethoxyphenyl)pyridine

HRID 322945Notes

Reaction equation

HRID 322945 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[O:11][CH3:12].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[Cl-]>O1CCCC1>[CH3:12][O:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 79732-BromopyridineHCID 872661-Bromo-2,4-dimethoxybenzeneHCID 5462224Magnesium

Product 1

HCID 108463432-(2,4-dimethoxyphenyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirred suspension of magnesium (8.11 g) in dry tetrahydrofuran (100 mL) is heated, and then treated with a solution of 1-bromo-2,4-dimethoxybenzene (48 mL) in tetrahydrofuran (100 mL) at such a rate as to maintain reflux. The resulting solution is then cooled and added, dropwise, to a solution of 2-bromopyridine (50.3 g) and bis-triphenylphosphinepalladium(II) chloride (3.5 g) in tetrahydrofuran (100 mL) at reflux, and the mixture is maintained at reflux for 6 hours. The solution is then evaporated and the residue is dissolved in ethyl acetate, washed with water, dried and evaporated to give a dark oil. This is subjected to flash chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (2:1 v/v) to give 2-(2,4-dimethoxyphenyl)pyridine (28 g) in the form of an oil. [NMR(CDCl3):- 3.84(3H,s),3.86(3H,s), 6.55(1H,s),6.6(1H,d),7.2(1H,m),7.7(1H,t),7.77 (1H,d),7.8(1H,d),8.7(1H,d)].

Workup

  1. temperatureis heated
  2. temperatureto maintain
  3. temperaturereflux
  4. temperatureThe resulting solution is then cooled
  5. additionadded
  6. temperaturethe mixture is maintained
  7. temperatureat reflux for 6 hours
  8. customThe solution is then evaporated
  9. dissolutionthe residue is dissolved in ethyl acetate
  10. washwashed with water
  11. customdried
  12. customevaporated
  13. customto give a dark oil
  14. washeluting with a mixture of pentane and ethyl acetate (2:1 v/v)

Sources & evidence

ORD record
ord-81a6cb67e54d4fb090bbde4e6a5f5d70
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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