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

HRID 1839147ノート

反応式

HRID 1839147 の反応式
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

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 693532,5-DibromopyridineHCID 178418816HCID 178418816、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178477753HCID 178477753、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-171334863de84634a284764fd662c287
出典データセット
uspto-grants-2004_01
特許番号
US06677351B2

反応ノート

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