Ethanol → 2-Fluoro-6-octyloxy3-(4-octyloxyphenyl)pyridine

HRID 1780553

Reaktionsgleichung

Reaktionsgleichung von HRID 1780553
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[C:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=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.C(OCC)C.O>[F:1][C:2]1[C:7]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:23][CH:22]=2)=[CH:6][CH:5]=[C:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:3]=1

Komponenten

9

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 145298p-Bromophenyl octyl etherHCID 190469402-Fluoro-6-octyloxypyridine-3-boronic acid

Produkt 1

HCID 190469692-Fluoro-6-octyloxy3-(4-octyloxyphenyl)pyridineAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2.00 g (7.44 mmol) of 2-fluoro-6-octyloxypyridine-3-boronic acid, 1.64 g (5.72 mmol) of 1-bromo-4-octyloxybenzene, 0.26 g (0.22 mmol) of tetrakis(triphenylphosphine)palladium(0) and 11.16 ml (22.32 mmol) of 2-molar sodium carbonate solution are refluxed in 20 ml of benzene and 10 ml of ethanol for 6 hours. After distributing the reaction mixture between water and diethyl ether, the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography (silica gel, 95:5 hexane/ethyl acetate) and recrystallization from acetonitrile give 1.02 g of 2-fluoro-6-octyloxy3-(4-octyloxyphenyl)pyridine. ##STR23##

Aufarbeitung

  1. washthe organic phase is washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue
  6. customby chromatography (silica gel, 95:5 hexane/ethyl acetate) and recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-dbb292851d0f40bdbc3c5e9e4eedc4a7
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05630962

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