4-Bromoanisole → 2-(4-methoxyphenyl)thiophene

Temperature

-20 °C

23.30 g of thiophene (0.277 mole) and 140 ml of dry THF were introduced into a 500 ml three-necked round bottom flask placed under nitrogen; after cooling to -20° C., 160 ml of butyllithium (46 M/1 in hexane) were run in slowly; the temperature was allowed to return to 0° C.; time 2 hours 30 min. 34.6 g (0.254 M) of ZnCl2 and 275 ml of dry THF were charged under nitrogen into a one-liter three-necked vessel with mechanical stirring. After allowing to dissolve, the above solution was run in over 30 min; the reaction was slightly exothermic. 20 ml of THF were added again for rinsing. 0.3907 g (6.80 ×10-4 mole) of Pd(DBA)2, 0.714 g (2.72 ×103 mole) of TPP and 220 ml of dry THF were charged into a 2 liter three-necked vessel placed under nitrogen; after allowing to react (10 min), 45.9 g (0.245 mole) of para-bromoanisole were added and the above solution was run in at normal temperature; heating under reflux was carried out for 16 hours. After allowing to cool, water was added and the mixture was extracted with ethyl acetate; the material was washed with water, dried over MgSO4 and was evaporated down; a solid was recovered. 27.3 g of a solid were obtained by recrystallization (melting point: 111° C.) (2-paramethoxyphenylthiophene).

1. customto return to 0° C.
2. customtime 2 hours 30 min
3. dissolutionto dissolve
4. customwas run in over 30 min
5. washfor rinsing
6. additionwere added
7. temperatureheating
8. temperatureunder reflux
9. temperatureto cool
10. extractionthe mixture was extracted with ethyl acetate
11. washthe material was washed with water
12. dry with materialdried over MgSO4
13. customwas evaporated down
14. customa solid was recovered

ORD record

ord-c98edbc58b6a4f7a910b08969ff0c852

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05156774