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

HRID 971097노트

반응식

HRID 971097 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

반응 조건

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-4a152df5d4e64ca68c041a69d6be4b3e
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312334B2

반응 노트

불러오는 중…