Dichloromethane → 1,4-Di(2-fluoro-6-octyloxypyridine-3-yl)benzene

HRID 1780560Notes

Reaction equation

HRID 1780560 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[F:9][C:10]1[C:15](B(O)O)=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:11]=1.[C:28](=[O:31])([O-])[O-].[Na+].[Na+].ClCCl>C1C=CC=CC=1.C(O)C.O.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>[F:9][C:10]1[C:15]([C:2]2[CH:7]=[CH:6][C:5]([C:15]3[C:10]([F:9])=[N:11][C:12]([O:31][CH2:28][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])=[CH:13][CH:14]=3)=[CH:4][CH:3]=2)=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:11]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 78041,4-DibromobenzeneHCID 10340Sodium CarbonateHCID 190469402-Fluoro-6-octyloxypyridine-3-boronic acid

Product 1

HCID 190469471,4-Di(2-fluoro-6-octyloxypyridine-3-yl)benzeneYield 79.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

0.87 g (3.7 mmol) of 1,4-dibromobenzene, 2.00 g (7.4 mmol) of 2-fluoro-6-octyloxypyridin-3-boronic acid (prepared as described in Example 5), 0.56 g (0.46 mmol) of tetrakis(triphenylphosphine)palladium(0) and 5 g (46.1 mmol) of sodium carbonate in 50 ml of benzene, 35 ml of ethanol and 20 ml of water are refluxed for 18 hours. After distributing the reaction mixture between water and dichloromethane, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography (silica gel, CH2Cl2) and recrystallization from acetonitrile give 1.55 g of 1,4-di(2-fluoro-6-octyloxypyridine-3-yl)benzene. ##STR36##

Workup

  1. washthe organic phase is washed with sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue
  6. customby chromatography (silica gel, CH2Cl2) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-a15a2e58252f4142aacc79a69cef98ad
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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