反応 #42153

反応方程式

ammonium chloride

tetrahydrofuran

phenylmagnesium chloride

4-chlorobenzonitrile

→

4-cyanobiphenyl

溶媒

N-methylpyrrolidinone

toluene

反応条件

後処理

1. 1
   その他A 50-ml four-necked flask was equipped with a stirrer
2. 2
   その他The flask was purged with argon
3. 3
   workup.STIRRINGby stirring at 25° C. for 30 minutes
4. 4
   その他The reaction liquid
5. 5
   その他previously obtained
6. 6
   workup.ADDITIONwas added
7. 7
   workup.STIRRINGby stirring at 25° C. for 30 minutes
8. 8
   workup.STIRRINGby stirring at 120° C. for 9 hours
9. 9
   workup.ADDITIONwere added
10. 10
    その他followed by separation
11. 11
    その他The organic phase was purified by column chromatography

実験手順

A 50-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 1.090 g (8 mmol) of zinc chloride and 4 ml of N-methylpyrrolidinone were weighed in the flask. The flask was purged with argon, followed by stirring. 3.4 ml (7.5 mmol) of 2.2M tetrahydrofuran solution of phenylmagnesium chloride was added dropwise at 25° C. over a period of 30 minutes, followed by stirring at 25° C. for 30 minutes. The reaction liquid previously obtained was added, followed by stirring at 25° C. for 30 minutes. Further, 0.688 g (5 mmol) of 4-chlorobenzonitrile was added, followed by stirring at 120° C. for 9 hours. After the completion of the reaction, 10 ml of toluene and 10 ml of saturated aqueous ammonium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.670 g of 4-cyanobiphenyl (yield: 75 mol % based on 4-chlorobenzonitrile). The identification of the product was made by mass spectroscopy.

出典