反应详情

n-Butyllithium (33.3 cm3 of a 1.5M solution in n-hexane) was added dropwise at -70° to a stirred solution of 4-bromoanisole (6.26 cm3) in THF (70 cm3) under nitrogen. After ten minutes, a solution of anhydrous zinc chloride (6.814 g) in THF (50 cm3) was added and the mixture was allowed to warm to room temperature over 0.5 hour. A mixture of 6-bromo-2-methoxy-8-methylquinoline (12.8 g) and tetrakis(triphenylphosphine)palladium (0) (0.5 g) was added and the mixture heated under reflux for 2 hours. Volatile material was removed in vacuo and the residue was partitioned between chloroform (150 cm3) and a solution of ethylenediaminetetraacetic acid (40 g) in water (250 cm3). The organic layer was dried (MgSO4) and evaporated to afford an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with hexane:ethyl acetate, 19:1. Combination and evaporation of the appropriate fractions afforded the title compound (5.49 g). A small portion of this was recrystallised from methanol and had m.p. of 104°-106° and the following analysis:

1. waitAfter ten minutes
2. additionwas added
3. temperaturethe mixture heated
4. temperatureunder reflux for 2 hours
5. customVolatile material was removed in vacuo
6. customthe residue was partitioned between chloroform (150 cm3)
7. dry with materialThe organic layer was dried (MgSO4)
8. customevaporated
9. customto afford an oil which
10. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
11. washeluting with hexane
12. customCombination and evaporation of the appropriate fractions