2-Bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazine → 2-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyrazine

HRID 864266

Reaktionsgleichung

Reaktionsgleichung von HRID 864266
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[C:12]1[C:17]([F:18])=[N:16][C:15]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:21][CH:20]=2)=[CH:14][N:13]=1>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[F:18][C:17]1[C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:13][CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:21][CH:20]=2)[N:16]=1

Komponenten

5

Edukt 2

HCID 218046332-Bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazineHCID 178443577HCID 178443577, Verbindung

Produkt 1

HCID 194182962-Fluoro-3-octyl-6-(4-octyloxyphenyl)pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

7.95 mmol of freshly prepared octylmagnesium bromide in 30 ml of tetrahydrofuran are added dropwise at -10° C. to 2.00 g (5.3 mmol) of 2-bromo-3-fluoro-5-(4-octyloxyphenyl)pyrazine and 0.03 g (0.06 mmol) of [1,3-bis-(diphenylphosphino)propane]nickel(II) chloride in 30 ml of tetrahydrofuran, and the reaction mixture is stirred overnight, during which it warms to room temperature. The reaction mixture is partitioned between aqueous ammonium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, filtered and freed from the solvent, and the mixture is purified by chromatography (silica gel/dichloromethane: hexane = 7:3). 1.12 g of 2-fluoro-3-octyl-6-(4-octyloxyphenyl)pyrazine are obtained. ##STR17## The compound has the following phase sequence:

Aufarbeitung

  1. customwarms to room temperature
  2. customThe reaction mixture is partitioned between aqueous ammonium chloride solution and ether
  3. washthe organic phase is washed with aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe mixture is purified by chromatography (silica gel/dichloromethane: hexane = 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-acb452673ccb482b9d8959684f9ae9c6
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05562859

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