2,6-Difluoropyridine → 2-Fluoro-6-[4-(4-octyloxyphenyl)phenyl]pyridine

HRID 1780554Notes

Reaction equation

HRID 1780554 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](F)[N:30]=1>CCCCCC.C1C=CC=CC=1.O1CCCC1>[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[N:30]=1

Participants

7

Reactant 3

HCID 739342,6-DifluoropyridineHCID 28017871-Bromo-4-(4-octoxyphenyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 190469542-Fluoro-6-[4-(4-octyloxyphenyl)phenyl]pyridineYield 25.5%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

24.00 g (66.60 mmol) of 4-bromo-4'-octyloxybiphenyl in 500 ml of hexane and 160 ml of benzene are stirred at room temperature with 49 ml (78.70 mmol) of a 1.6-molar n-butyllithium solution in hexane under argon for 18 hours. The reaction mixture is then slowly added dropwise at 0° C. under argon to a solution of 5.5 ml (60 mmol) of 2,6-difluoropyridine in 200 ml of tetrahydrofuran. After a reaction time of 5 hours at 0° C., the reaction mixture is evaporated to dryness, the residue is taken up in toluene, and solid components are filtered off. The filtrate is washed with water, dried over sodium sulfate, filtered and freed from solvent. Recrystallization from 8:2 hexane/ethyl acetate gives 5.77 g of 2-fluoro-6-[4-(4-octyloxyphenyl)phenyl]pyridine. ##STR24##

Workup

  1. customAfter a reaction time of 5 hours at 0° C., the reaction mixture is evaporated to dryness
  2. filtrationsolid components are filtered off
  3. washThe filtrate is washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customRecrystallization from 8:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-ce10c718f10e48648904e1ddf7698ed0
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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