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Triethyltin bromide → 2-Methyl-4-triethylstannyl-thiazole

HRID 2220119
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2220119
[CH3:1][C:2]1[S:3][CH:4]=[C:5](Br)[N:6]=1.C([Li])CCC.[CH2:13]([Sn:15](Br)([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14]>CCOCC>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([Sn:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:13][CH3:14])[N:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 17701Triethyltin bromideHCID 27631864-Bromo-2-methyl-1,3-thiazoleHCID 178418339Butyllithium

Produkt 1

HCID 689777192-Methyl-4-triethylstannyl-thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyllithium (1.6M, 3.3 mL, 5.35 mmol) was added to a solution of 2,4-dibromothiazole (1.0 g, 4.12 mmol) in anhydrous ether (10 mL) stirred at −78 ° C. under nitrogen. After 20 minutes, methyl trifluromethanesulfonate (878 mg, 5.35 mmol) was added, then the reaction mixture was allowed to warm to room temperature, and stirred for another 1 h. The mixture was quenched and washed with water, washed with brine, dried through MgSO4, and then the solvent was evaporated to give a brown oily residue of 2-methyl-4-bromo-thiazole (900 mg). Under nitrogen, the 2-methyl-4-bromo-thiazole (430 mg, 2.42 mmol) dissolved in anhydrous ether (5 mL) then cooled to −78° C. under nitrogen. n-Butyllithium (1.6M, 1.7 mL, 2.66 mmol) was added, followed, after 10 min by triethylstannyl bromide (760 mg, 2.66 mmol). The solution was then warmed to room temperature, and stirred for another 1 h. The mixture was quenched, and washed with 1N sodium hydroxide, dried through MgSO4, and then the solvent was evaporated to give the sub-title compound give as a brown oily residue (655 mg), which was used without further purification in the next step.

Aufarbeitung

  1. temperatureThe solution was then warmed to room temperature
  2. customThe mixture was quenched
  3. washwashed with 1N sodium hydroxide
  4. dry with materialdried through MgSO4
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-0b272f7fd4a84741bfc9a56ac4cb5921
Quelldatensatz
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07417050B2

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