1-Octanol → 5-Bromo-3-fluoro-2-octyloxypyridine

HRID 1757360Notes

Reaction equation

HRID 1757360 reaction equation
[CH2:1]([O-:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Li+].C(O)CCCCCCC.C([Li])CCC.Br[C:26]1[C:31]([F:32])=[CH:30][C:29]([Br:33])=[CH:28][N:27]=1>CCCCCC.O1CCCC1>[Br:33][C:29]1[CH:30]=[C:31]([F:32])[C:26]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:27][CH:28]=1

Participants

7

Reactant 4

HCID 9571-OctanolHCID 224128322,5-Dibromo-3-fluoropyridineHCID 23682185Lithium octanolateHCID 178418339Butyllithium

Product 1

HCID 193875335-Bromo-3-fluoro-2-octyloxypyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Lithium octanolate (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 at 0° C. in 40 ml of tetrahydrofuran) and 25.49 g (100.00 mmol) of 2,5-dibromo-3-fluoropyridine are refluxed for 7 hours in 40 ml of tetrahydrofuran. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, and the ether phase is washed twice with aqueous sodium chloride solution, dried over sodium sulfate, filtered and freed from solvent. Chromatographic purification (silica gel/hexane: ethyl acetate 9:1) gives 18.19 g (59.80 mmol) of 5-bromo-3-fluoro-2-octyloxypyridine. ##STR23##

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-eb063287efe544cabee688c57bbdab00
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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