Ethanol → 3-Chloro-2,5-di(4-octyloxyphenyl)pyridine

HRID 1780067

Reaction equation

HRID 1780067 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:23])[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)=[N:6][CH:7]=1.[CH2:24]([O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:23][C:4]1[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)=[N:6][CH:7]=[C:2]([C:36]2[CH:37]=[CH:38][C:33]([O:32][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:34][CH:35]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 190500045-Bromo-3-chloro-2-(4-octyloxyphenyl)pyridine

Product 1

HCID 190499933-Chloro-2,5-di(4-octyloxyphenyl)pyridineYield 48.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2.00 g (5.40 mmol) of 5-bromo-3-chloro-2-(4-octyloxyphenyl)pyridine, 1.50 g (6.00 mmol) of 4-octyloxybenzeneboronic acid, 0.07 g (0.6 mmol) of tetrakis(triphenylphosphine)palladium(0) and 1.3 g (12.00 mmol) of sodium carbonate are heated at 80° C. for 3 hours in 20 ml of toluene, 10 ml of ethanol and 10 ml of water. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and evaporated, and the product is purified by chromatography (silica gel/dichloromethane), giving 1.38 g of 3-chloro-2,5-di(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. customthe product is purified by chromatography (silica gel/dichloromethane)

Sources & evidence

ORD record
ord-6369c675c53c486b9e2852c43191dc58
Source dataset
uspto-grants-1997_05
Patent number
US05629428

Linked notes

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