Réaction #57309

Équation de réaction

1,6-dibromohexane

tetramethylpiperidine

compound

4′-methyl-2,2′;6,2″-terpyridine

compound 221

4′-methyl-2,2′;6,2″-terpyridine

normal butyllithium

→

compound 231

4′-(7-bromoheptyl)-2,2′;6′,2″-terpyridine

Solvants

THF

THF

THF

ethylacetate

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwise slowly
2. 2
   workup.STIRRINGAfter being stirred at −78□ for 30 minutes
3. 3
   workup.ADDITIONwas diluted
4. 4
   workup.STIRRINGAfter being stirred at −78□ for 12 hours
5. 5
   workup.DISTILLATIONthe resultant material was distilled under reduced pressure

Mode opératoire

0.5 ml of tetramethylpiperidine (3 mmol) and 20 ml of anhydrous THF were put into a 100 ml Schlenk flask and stirred well. After the resultant material was cooled using liquid nitrogen and ethylacetate to −78□, 1.88 mL of normal butyllithium (3 mmol, 1.6 M hexane solution) was added dropwise slowly using an injector. 15 ml of THF, in which 0.5 g of the compound synthesized in Example 2 (compound 221 in FIG. 2, 2 mmol) was dissolved, was put into the flask using an injector at −78□. After being stirred at −78□ for 30 minutes, the resultant material was added dropwise slowly into 1 ml of a 1,6-dibromohexane solution (4 mmol), in which 50 ml of THF was diluted, using a cannula at −78□. After being stirred at −78□ for 12 hours, the resultant material was distilled under reduced pressure to be a saturation solution. Next, the resultant material was refined using column chromatography (developer: THF/normal hexane=⅓) to obtain a compound 4′-(7-bromoheptyl)-2,2′;6′,2″-terpyridine (intermediate compound 231 in FIG. 2) with a yield of 76%.

Source