Benzyl Bromide → 2-Benzyl-3-methoxymethyloxypyridine

HRID 2216346Notes

Reaction equation

HRID 2216346 reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:12]([Mg]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Br)C1C=CC=CC=1.[Mg].[Cl-].[NH4+]>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].C(OCC)C.O1CCCC1>[CH2:12]([C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 115865732-Bromo-3-(methoxymethoxy)pyridineHCID 178419663HCID 178419663, compound

Product 1

HCID 219422452-Benzyl-3-methoxymethyloxypyridine

Reagents, catalysts & solvents 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideCatalystHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

While stirring a mixture of 35 g of 2-bromo-3-methoxymethyloxypyridine, 5 g of 1,3-bis(diphenylphosphino)propanenickel (II) chloride and 200 ml of tetrahydrofuran under ice-cooling, a diethyl ether solution of benzylmagnesium bromide prepared from 38 ml of benzyl bromide, 8 g of magnesium and 250 ml of anhydrous diethyl ether was slowly added dropwise thereinto under nitrogen atmosphere. After stirring for 4.5 hours, a saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (8–20% ethyl acetate/hexane), to give 27 g of the title compound.

Workup

  1. temperaturecooling
  2. additionwas slowly added dropwise
  3. stirringAfter stirring for 4.5 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel column chromatography (8–20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fdd3ab66e2b4417387cc9bcbd17d684f
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

Loading…