反应详情

温度

-40 °C

A stirred suspension of magnesium turnings (3.4 g, 142 mmol) in diethyl ether (20 ml) was added a solution of 1-bromo-3,4-dichlorobenzene (29 g, 130 mmol) in diethyl ether (150 ml). The mixture was heated at reflux for 20 minutes and then cooled at −40° C. A solution of arecoline (10 g, 65 mmol) in toluene (100 ml) was added slowly while keeping the internal temperature between −40° C. and −30° C. The reaction mixture was stirred at −20° C. for 6 hours and then added 4 N HCl (50 ml). The phases were then separated and the aqueous phase was added ammonia (aq) until basic pH and extracted with dichloromethane (4×100 ml), dried with magnesium sulfate and evaporated to an oil. The isomers (1) and (2) were separated by column chromatography (petroleum ether, ether, triethylamine 70:25:5) to give 5.0 g (25%) of (1) (mp. 70-75° C.) and 2.0 g (10%) of (2) (oil).

1. temperatureThe mixture was heated
2. temperatureat reflux for 20 minutes
3. customthe internal temperature between −40° C. and −30° C
4. customThe phases were then separated
5. additionthe aqueous phase was added ammonia (aq) until basic pH
6. extractionextracted with dichloromethane (4×100 ml)
7. dry with materialdried with magnesium sulfate
8. customevaporated to an oil
9. customThe isomers (1) and (2) were separated by column chromatography (petroleum ether, ether, triethylamine 70:25:5)