Reaktion #610322

Reaktionsgleichung

CH2Cl2

thiazol-2-ylzinc(II) bromide

THF

2,4,6-trichloropyridine

→

2-(4,6-dichloropyridin-2-yl)thiazole

Ausbeute 46.0%

Lösungsmittel

MeOH

water

NaCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 15 mL vial equipped with a stir bar
2. 2
   SonstigeThe vial was sealed with a septum screwcap
3. 3
   Sonstigewas placed in a 60° C.
4. 4
   Temperaturheating block
5. 5
   SonstigeThe reaction mixture was transfered to a separatory funnel
6. 6
   ExtraktionThe mixture was extracted with EtOAc
7. 7
   WaschenThe organic phase was washed with brine (25 mL)
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Einengenthen concentrated in vacuo
11. 11
    Sonstigeto afford an orange solid

Vorschrift

To a 15 mL vial equipped with a stir bar was added 2,4,6-trichloropyridine (182 mg, 1.00 mmol) and Pd(dppf)Cl2 (73.2 mg, 0.100 mmol). The vial was sealed with a septum screwcap and was then placed under N2 atmosphere. To the vial was added thiazol-2-ylzinc(II) bromide in THF (8.00 mL, 4.00 mmol). The vial was placed in a 60° C. heating block with stirring for 3 h. The reaction mixture was transfered to a separatory funnel and diluted with water (25 mL) and sat. aq. NaCl (“brine”, 25 mL). The mixture was extracted with EtOAc:Et2O (40 mL:20 mL). The organic phase was washed with brine (25 mL); dried over MgSO4; filtered; then concentrated in vacuo to afford an orange solid. This material was subjected to silica gel chromatography (CH2Cl2:MeOH, 100:0 to 99:1) to afford 2-(4,6-dichloropyridin-2-yl)thiazole as a white solid (231 mg, 46%). 1H-NMR (400 MHz, CDCl3) δ 8.16 (d, J=1.8 Hz, 1H), 7.95 (d, J=3.3 Hz, 1H), 7.52 (d, J=3.0 Hz, 1H), 7.37 (d, J=1.8 Hz, 1H).

Quelle