Réaction #12060

Équation de réaction

benzyl magnesium chloride

2-bromo-indene

→

2-benzylindene

Solvants

ether

diethyl ether

—

hexanes

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was heated
2. 2
   Températureto reflux overnight
3. 3
   Autrequenched
4. 4
   workup.ADDITIONadding 150 mL of 1.0 M aqueous hydrochloric acid
5. 5
   AutreThe organic layer was separated
6. 6
   Lavagewashed twice with 50 mL of ether
7. 7
   Séchagedried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Autrethe volatiles removed in vacuo
10. 10
    Autreto leave a dark oil
11. 11
    Autrepurified by flash column chromatography

Mode opératoire

A 500 mL 3 neck flask was charged with 2.5 g (13 mmol) of 2-bromo-indene, 50 mg of NiCl2(1,3-bis(diphenylphosphino)propane) (0.06 mmol) and 150 mL of diethyl ether. To this mixture was added dropwise 12.8 mL of 1.0 M benzyl magnesium chloride in ether (12.8 mmol). The reaction was heated to reflux overnight and then quenched by cooling to 0° C. and adding 150 mL of 1.0 M aqueous hydrochloric acid. The organic layer was separated and washed twice with 50 mL of ether. The organic extracts were combined, dried over magnesium sulfate, filtered and the volatiles removed in vacuo to leave a dark oil. The sample was dissolved in a small amount of hexanes and purified by flash column chromatography using silica and hexanes as the elutent. Yield: 1.75 g, 66 percent

Source