Diethyl Ether → 5-Bromo-2-(2-methylpropyl)pyridine

HRID 1839147노트

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HRID 1839147 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([Mg]Br)[CH:10]([CH3:12])[CH3:11].CCOCC>O1CCCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl.[Fe]>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:9][CH:10]([CH3:12])[CH3:11])=[N:3][CH:4]=1

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 693532,5-DibromopyridineHCID 178418816HCID 178418816, 화합물

생성물 1

HCID 223920125-Bromo-2-(2-methylpropyl)pyridine

시약·촉매·용매 2

HCID 178477753HCID 178477753, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

To a solution of 2,5-dibromopyridine (4.5 g, 19 mmol) in tetrahydrofuran (50 ml) was added [1,1′-bis (diphenylphosphino)ferrocene]dichloronickel (II) (103 mg, 0.19 mmol) and the resulting mixture was cooled to −10° C. A 2M solution of isobutylmagnesium bromide in ether (12.4 ml, 24.7 mmol) was added slowly and the mixture was stirred at −10 to 10° C for 3.5 hours. After quenching with saturated aqueous ammonium chloride solution, the mixture was partitioned between ether and water and the product from the organic phase was chromatographed on silica gel eluting with 10% ether in pentane to afford the 5-Bromo-2-(2-methylpropyl)pyridine compound as a volatile oil.

후처리

  1. customAfter quenching with saturated aqueous ammonium chloride solution
  2. customthe mixture was partitioned between ether and water
  3. customthe product from the organic phase was chromatographed on silica gel eluting with 10% ether in pentane

출처 및 근거

ORD 기록
ord-171334863de84634a284764fd662c287
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677351B2

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