Reaktion #51197

Reaktionsgleichung

nBuLi

1,4-dibromobenzene

2-bromopyridine

→

title product

Ausbeute 71.0%

2-(4-Bromophenyl)-pyridine

Ausbeute 71.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Sonstigeevaporated to low (10 ml) volume
3. 3
   workup.ADDITIONdiluted with EtOAc (400 ml)
4. 4
   WaschenThe solution was washed with a solution of 32 g of EDTA in 200 ml water and brine (200 ml)
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated to a yellow/green solid
7. 7
   SonstigeThis solid was purified by column chromatography

Vorschrift

nBuLi (1.6M in hexanes, 34.4 mls, 55 mmol) was added dropwise to a stirred solution of 1,4-dibromobenzene (11.8 g, 50 mmol) in 100 ml of dry THF at −60° C. The mixture was stirred for 15 min at this temperature before a solution of ZnCl2 (0.5M in THF, 100 ml, 50 mmol) in THF was added dropwise. The mixture was allowed to warm to room temperature over 90 min, and then Pd(PPh3)4 (200 mg) was added, followed immediately by 2-bromopyridine (4.8 ml, 50 mmol). The whole was stirred at room temperature overnight, then evaporated to low (10 ml) volume and diluted with EtOAc (400 ml). The solution was washed with a solution of 32 g of EDTA in 200 ml water and brine (200 ml), dried (MgSO4) and evaporated to a yellow/green solid. This solid was purified by column chromatography using 1:1 hexane:DCM as eluant to provide the title product (8.3 g; 71%); m/z MH+ 234 (TS+); Found C, 56.61%, H, 3.37%, N, 5.90%; Calcd. C, 56.44%, H, 3.44%, N, 5.98%.

Quelle