1-Octanol → 5-Bromo-3-chloro-2-(octyloxy)pyridine

HRID 1780065노트

반응식

HRID 1780065 반응식
[C:1]([O-:10])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Li+].C(O)CCCCCCC.C([Li])CCC.Br[C:27]1[C:32]([Cl:33])=[CH:31][C:30]([Br:34])=[CH:29][N:28]=1>CCCCCC.O1CCCC1>[Br:34][C:30]1[CH:31]=[C:32]([Cl:33])[C:27]([O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:28][CH:29]=1

참가 물질

7

반응물 4

HCID 9571-OctanolHCID 126309832,5-Dibromo-3-chloropyridineHCID 23673717Octanoic acid, lithium salt (1:1)HCID 178418339Butyllithium

생성물 1

HCID 190499905-Bromo-3-chloro-2-(octyloxy)pyridine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

Lithium octanoate (prepared in advance from 13.02 g (100.00 mmol) of 1-octanol and 69 ml (110.00 mmol) of a 1.6 molar n-butyllithium solution in n-hexane in 40 ml of tetrahydrofuran at 0° C.) and 27.13 g (100.00 mmol) of 2,5-dibromo-3-chloropyridine are refluxed for 7 hours in 40 ml of tetrahydrofuran. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, the ether phase is washed twice with aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the filtrate is freed from the solvent. Chromatographic purification (silica gel/hexane:ethyl acetate 9:1) gives 18.19 g (59.80 mmol) of 5-bromo-3-chloro-2-octyloxypyridine. ##STR21##

후처리

  1. customThe mixture is subsequently partitioned between aqueous sodium chloride solution and ether
  2. washthe ether phase is washed twice with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customChromatographic purification (silica gel/hexane:ethyl acetate 9:1)

출처 및 근거

ORD 기록
ord-8c7820111dee488d957c382dab128453
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629428

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