Pyridine → 2-Bromo-4-(1-bromoethyl)-1,3-thiazole

HRID 1042340

Reaktionsgleichung

Reaktionsgleichung von HRID 1042340
S(Br)([Br:3])=O.[Br:5][C:6]1[S:7][CH:8]=[C:9]([CH:11](O)[CH3:12])[N:10]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[S:7][CH:8]=[C:9]([CH:11]([Br:3])[CH3:12])[N:10]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 668613171-(2-Bromothiazol-4-yl)ethan-1-ol

Produkt 1

HCID 668607482-Bromo-4-(1-bromoethyl)-1,3-thiazoleAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution thionyl bromide (0.787 g, 3.78 mmol, 1.05 eq.) in 20 ml dry DCM, cooled to 5° C., was added dropwise a solution of 1-(2-bromo-1,3-thiazol-4-yl)ethanol (0.75 g, 3.60 mmol, 1 eq.) and pyridine (0.285 g, 3.60 mmol, 1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred 1.5 hr. 100 ml of water and 100 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried of MgSO4 and evaporated to give 2-bromo-4-(1-bromoethyl)-1,3-thiazole (0.9 g, 84% yield) as a yellow viscous oil.

Aufarbeitung

  1. additionOn complete addition
  2. customthe cooling bath was removed
  3. addition100 ml of water and 100 ml of DCM were added
  4. stirringstirring
  5. waitallowed for 2 mins
  6. customThe organic layer was separated
  7. dry with materialdried of MgSO4
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6ae5e7cedafb4a5d9f9efd7e5a21f2fd
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557849B2

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