Reaktion #42151

Reaktionsgleichung

bromobenzene

4-vinylphenylmagnesium chloride

ammonium chloride

→

4-vinylbiphenyl

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 100-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   SonstigeThe flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 19° C. for 30 minutes
5. 5
   workup.STIRRINGby stirring at 19° C. for 30 minutes
6. 6
   workup.STIRRINGby stirring at 30° C. for 2 hours
7. 7
   workup.ADDITIONwas added
8. 8
   Sonstigefollowed by separation
9. 9
   SonstigeThe organic phase was purified by column chromatography

Vorschrift

A 100-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 0.0674 g (0.3 mmol) of palladium (II) acetate and 6 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.314 g (0.6 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 19° C. for 30 minutes. 4.710 g (30 mmol) of bromobenzene was added, followed by stirring at 19° C. for 30 minutes. 40 ml (50 mmol) of 1.25M tetrahydrofuran solution of 4-vinylphenylmagnesium chloride was added dropwise at 19° C. over a period of 2 hours, followed by stirring at 30° C. for 2 hours. After the completion of the reaction, 10 ml of saturated aqueous ammonium chloride solution was added, followed by separation. The organic phase was purified by column chromatography to afford 4.450 g of 4-vinylbiphenyl (yield: 82 mol % based on bromobenzene). The identification of the product was made by mass spectroscopy.

Quelle