Ethanol → 3-Fluoro-2-octyloxy-5-(4-octyloxyphenyl)pyridine

HRID 1757361Notes

Reaction equation

HRID 1757361 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:17])[C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:6][CH:7]=1.[CH2:18]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.O>[F:17][C:4]1[C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:6][CH:7]=[C:2]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:28][CH:29]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 193875335-Bromo-3-fluoro-2-octyloxypyridine

Product 1

HCID 193875393-Fluoro-2-octyloxy-5-(4-octyloxyphenyl)pyridineYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3.00 g (9.86 mmol) of 5-bromo-3-fluoro-2-octyloxypyridine, 2.47 g (9.86 mmol) of 4-octyloxybenzeneboronic acid, 0.11 g (0.10 mmol) of tetrakis(triphenylphospine)palladium(0) and 2.09 g (19.72 mmol) of sodium carbonate are heated at 80° C. for 3 hours in 90 ml of toluene, 60 ml of ethanol and 30 ml of water. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether and the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, evaporated and purified by chromatography (silica gel/hexane: ethyl acetate 9:1), giving 2.85 g of 3-fluoro-2-octyloxy-5-(4-octyloxyphenyl)pyridine. ##STR24##

Workup

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

Sources & evidence

ORD record
ord-912fc48d087a41629a6deb44dd8ed11c
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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