3-Bromo-2-ethoxypyridine → 5,5'-Bis[2-ethoxypyridine]

HRID 404526

Reaktionsgleichung

Reaktionsgleichung von HRID 404526
Br[C:2]1[C:3]([O:8][CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1>[N+](CC)(CC)(CC)CC.[I-].C1COCC1.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[CH2:9]([O:8][C:3]1[N:4]=[CH:5][C:6]([C:6]2[CH:5]=[N:4][C:3]([O:8][CH2:9][CH3:10])=[CH:2][CH:7]=2)=[CH:7][CH:2]=1)[CH3:10]

Komponenten

6

Edukt 1

HCID 109873083-Bromo-2-ethoxypyridine

Produkt 1

HCID 8247525,5'-Bis[2-ethoxypyridine]

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6225Tetraethylammonium IodideKatalysatorHCID 23994ZincKatalysatorHCID 178418751HCID 178418751, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The title compound was prepared as described by Constable et al.13 using NiCl2(PPh3)2 (327 mg, 0.5 mmol, 0.3 eq.), acid washed Zn powder (164 mg, 1.5 eq.) and Et4NI (435 mg, 1.7 mmol, 1 eq.) in. distilled THF (10 mL). with a solution of 5 bromo-2 ethoxypyridine (344 mg, 1.7 mmol, 1 eq.) in THF (5 mL) at 50° C. for 24 h. Workup gave a white crystalline solid (237 mg; 80%). The reaction was also carried out on a larger scale (1.0 g or 1.7 g of starting material) giving yields of 85% and 90% respectively. The spectral data were consistent with literature data13.

Aufarbeitung

  1. customWorkup gave a white crystalline solid (237 mg; 80%)
  2. customgiving
  3. customyields of 85% and 90% respectively

Quellen und Nachweise

ORD-Eintrag
ord-ff3335dd637e438d845ea43517055040
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748582B2

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