Dichloromethane → 3,5-Dibromo-2-chloropyrazine

HRID 57935

Reaktionsgleichung

Reaktionsgleichung von HRID 57935
[Br:1][C:2]1[C:3](N)=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.N(OC(C)(C)C)=O.[Cl:17]CCl>[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:17])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1

Komponenten

5

Edukt 3

HCID 6344Dichloromethane2×HCID 10906Tert-Butyl nitriteHCID 6200042-Amino-3,5-dibromopyrazine

Produkt 1

HCID 533503583,5-Dibromo-2-chloropyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24193Titanium TetrachlorideKatalysator

Versuchsvorschrift

To a solution of 3,5-dibromopyrazin-2-amine (1.00 g, 3.95 mmol) in dichloromethane 6.0 ml at 0° C. was added titanium tetrachloride (1 mol/l) in dichloromethane (3.95 mL, 3.95 mmol) then tert-butyl nitrite (1.05 mL, 7.91 mmol) was added dropwise. The reaction was warmed to RT then 1 more equivalent of TiCL4 was added and stirred for 1 h. The reaction was quenched with water and extracted with DCM. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was carried to next step. MS (ESI) m/z: 272.2.

Aufarbeitung

  1. addition1 more equivalent of TiCL4 was added
  2. customThe reaction was quenched with water
  3. extractionextracted with DCM
  4. dry with materialThe organic layers was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7aed7c16ee7542eb8f1c3f5607bec920
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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