1,4-Dibromobenzene → HCID 19017168, Verbindung

HRID 1728272

Reaktionsgleichung

Reaktionsgleichung von HRID 1728272
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.C[Si](C)(C)[O:12][C:13]1[CH:14]=[CH:15][C:16](Cl)=[N:17][CH:18]=1.C(=O)([O-])O.[Na+]>C(OCC)C.CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].O1CCCC1>[OH:12][C:13]1[CH:14]=[CH:15][C:16]([C:3]2[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=2)=[N:17][CH:18]=1

Komponenten

8

Edukt 4

HCID 78041,4-DibromobenzeneHCID 516892Sodium BicarbonateHCID 5462224MagnesiumHCID 19017088HCID 19017088, Verbindung

Produkt 1

HCID 19017168HCID 19017168, VerbindungAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A Grignard reagent solution prepared from 0.8 g of magnesium, 8.0 g of 1,4-dibromobenzene and 50 ml of tetrahydrofuran was added dropwise at 0°-5° C. within 30 minutes to a mixture of 6.6 g of 5-trimethylsilyloxy-2-chloropyridine, 75 ml of tetrahydrofuran and 0.4 g of 1,3-bis(diphenylphosphino)-propanenickel(II) chloride. The reaction mixture was stirred for 3 hours, left to stand overnight, then adjusted to pH 8 with aqueous sodium hydrogen carbonate solution and diluted with diethyl ether. The organic phase was washed neutral with water, dried over sodium sulfate and concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) yielded 5.5 g of 5-hydroxy-2-(4-bromophenyl)-pyridine.

Aufarbeitung

  1. waitleft
  2. waitto stand overnight
  3. washThe organic phase was washed neutral with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customChromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7bf43c9387e74ea98eb45762e01f3f7d
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326497

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