Sodium Fluoride → 2-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyridine

HRID 1780545Notes

Reaction equation

HRID 1780545 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:6][CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=2)[N:3]=1.[F-:31].[K+].[F-].[Na+].C1OCCOCCOCCOCCOCCOC1>CCOCC.O>[F:31][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:6][CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 5235Sodium FluorideHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 190469532-Chloro-3-octyl-6-(4-octyloxyphenyl)pyridine

Product 1

HCID 190469322-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyridineYield 53.2%

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

0.20 g (0.5 mmol) of 2-chloro-3-octyl-6-(4-octyloxyphenyl)pyridine is heated together with 0.5 g of potassium fluoride, 0.5 g sodium fluoride and 0.02 g of 18-crown-6 in a sealed tube at 200° C. for 18 hours. The reaction mixture is taken up in ether/water, the organic phase is washed with water, dried over sodium sulfate, filtered, the solvent is distilled off, the residue is purified by chromatography (silica gel, 8:2 hexane/ethyl acetate) and recrystallized from acetonitrile, giving 0.11 g of 2-fluoro-3-octyl-6- (4-octyloxyphenyl ) pyridine. ##STR16##

Workup

  1. washthe organic phase is washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. distillationthe solvent is distilled off
  5. customthe residue is purified by chromatography (silica gel, 8:2 hexane/ethyl acetate)
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-710e673a23d24233b5887d8b6ecefbc5
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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