Benzyl Bromide → 2-Benzyl-6-methoxypyridine

HRID 2216338

Reaction equation

HRID 2216338 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.O1CCCC1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Mg]>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].C(OCC)C>[CH2:15]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 2568102-Bromo-6-methoxypyridineHCID 5462224Magnesium

Product 1

HCID 219422742-Benzyl-6-methoxypyridine

Reagents, catalysts & solvents 2

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

While stirring a mixture of 150 g of 2-bromo-6-methoxypyridine, 4.3 g of 1,3-bis(diphenylphosphino)propanenickel (II) chloride and 500 ml of tetrahydrofuran in an ice bath, Grignard reagent prepared from 123 ml of benzyl bromide, 30 g of magnesium and 400 ml of diethyl ether was added dropwise slowly. After stirring overnight as it was, the mixture was extracted with an aqueous ammonium chloride solution and hexane. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column chromatography with (1% ethyl acetate/hexane and 1.5% ethyl acetate/hexane), to give 150 g of the title compound.

Workup

  1. additionwas added dropwise slowly
  2. stirringAfter stirring overnight as it
  3. extractionthe mixture was extracted with an aqueous ammonium chloride solution and hexane
  4. washThe organic layer was washed with water
  5. dry with materialwith brine, dried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by silica gel column chromatography with (1% ethyl acetate/hexane and 1.5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cb11222e764849c083897a8941c8501e
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Linked notes

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