Diethyl Ether → (4-Methoxyphenyl)(thiophen-3-yl)methanone

Temperature

-75 °C

To 4.0 g (0.0246 m) of 3-bromothiophene in 70 ml ether cooled to -75° C. under N2 was added dropwise 0.0246 m of n-butyllithium (in hexane) at such a rate that the temperature was <-70° C. After addition was complete the reaction mixture was stirred at -75° C. for 10 minutes and then a solution of 4-methoxybenzonitrile (3.46 g, 0.026 m) in 20 ml ether was added dropwise at <-70° C. The resulting suspension was stirred at -75° C. for 45 minutes and then allowed to warm to -10° C. over 2 hours. The reaction mixture was cooled, quenched with 15 ml H2O and then with 40 ml of 2N HCl. The phases were separated and the aqueous extract was washed with 50 ml ether, and then heated at reflux for 2 hours. This solution was cooled and extracted with 2×60 ml ether. The organic phases were washed with brine, dried and evaporated to give an oil which was triturated with petroleum ether to give the product as a solid, m.p. 58°-61° C.

1. customwas <-70° C
2. additionAfter addition
3. stirringThe resulting suspension was stirred at -75° C. for 45 minutes
4. temperatureto warm to -10° C. over 2 hours
5. temperatureThe reaction mixture was cooled
6. customquenched with 15 ml H2O
7. customThe phases were separated
8. extractionthe aqueous extract
9. washwas washed with 50 ml ether
10. temperatureheated
11. temperatureat reflux for 2 hours
12. temperatureThis solution was cooled
13. extractionextracted with 2×60 ml ether
14. washThe organic phases were washed with brine
15. customdried
16. customevaporated
17. customto give an oil which
18. customwas triturated with petroleum ether

ORD record

ord-a5190544a15947ae864a3c369229acbb

Source dataset

uspto-grants-1990_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04914111