1-Bromo-2,4-dimethoxybenzene → HCID 17968171, compound

HRID 271571

Reaction equation

HRID 271571 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].Cl.Br[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1>C1COCC1>[CH3:12][O:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 872661-Bromo-2,4-dimethoxybenzeneHCID 881004-Bromopyridinium chlorideHCID 5462224Magnesium

Product 1

HCID 17968171HCID 17968171, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The Grignard reagent, prepared from magnesium (5 g) and 1-Bromo-2,4-dimethoxybenzene (38 g) in THF (300 ml), is added at room temperature to 4-Bromo-pyridine hydrochloride salt in THF (10 ml). The mixture is heated under reflux for 2 hours and then evaporated to dryness. The residue is taken up in ethyl acetate and extracted with 1N hydrochloric acid. The aqueous phase is neutralised with 4M sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried with magnesium sulfate, evaporated and the residue is purified by column chromatography on silica gel using n-hexane:AcOEt=1:1 (v/v). MS-APCI+ (M+H)+=216

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated to dryness
  4. extractionextracted with 1N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried with magnesium sulfate
  7. customevaporated
  8. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5fa6046640ef4ac79636829ba2fcab2e
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Linked notes

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