Benzyl Bromide → 2-Benzyl-6-methoxypyridine

HRID 2216338

반응식

HRID 2216338 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 219422742-Benzyl-6-methoxypyridine

시약·촉매·용매 2

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chloride촉매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cb11222e764849c083897a8941c8501e
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112593B2

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