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

HRID 1780065Notes

Reaction equation

HRID 1780065 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

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##

Workup

  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)

Sources & evidence

ORD record
ord-8c7820111dee488d957c382dab128453
Source dataset
uspto-grants-1997_05
Patent number
US05629428

Reaction notes

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