1,1-Dibromoethane → Tributyl-(4-ethylphenyl)stannane

To a solution of magnesium (896 mg) in tetrahydrofuran (20 ml) was added dibromoethan (0.1 ml), and the mixture was stirred at room temperature for 15 minutes. Thereto was added dropwise a solution of 1-bromo-4-ethylbenzene (5.7 g) in tetrahydrofuran (20 ml), and subsequently, the mixture was stirred at room temperature for one hour. The reaction mixture was cooled to −78° C., and thereto was added dropwise tributyltin chloride (9.49 g). The mixture was stirred at the same temperature for 30 minutes, and then at room temperature for one hour. To the reaction mixture were added 10% aqueous potassium fluoride solution and ethyl acetate, and the mixture was stirred at room temperature for 30 minutes. Insoluble materials were filtered off. The organic layer of the filtrate was washed with water and brine successively, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by alumina column chromatography (hexane) to give the desired tri-n-butyl(4-ethylphenyl)tin (10.7 g) as colorless oil. EI-Mass m/Z 337 (M-Bu).

1. stirringsubsequently, the mixture was stirred at room temperature for one hour
2. temperatureThe reaction mixture was cooled to −78° C.
3. stirringThe mixture was stirred at the same temperature for 30 minutes
4. waitat room temperature for one hour
5. stirringthe mixture was stirred at room temperature for 30 minutes
6. filtrationInsoluble materials were filtered off
7. washThe organic layer of the filtrate was washed with water and brine successively
8. dry with materialdried over sodium sulfate
9. customThe solvent was evaporated under reduced pressure
10. customthe residue was purified by alumina column chromatography (hexane)

ORD-Eintrag

ord-99bc2f8f412b49c5965786b6e664c47f

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08785403B2