反应详情

A solution of (4-chlorophenyl)magnesium bromide (2.02 mL, 1.0 M in THF) was dropwise added to a suspension of methyl 4,8-dibromoquinoline-6-carboxylate (0.2 g, 0.58 mmol) in THF (5 mL) at room temperature. The resulting mixture was slowly dissolved and became a clear solution after 30 min. During this period of time, cooling was needed, when the temperature of the reaction mixture rose above room temperature. After 2 hr, the reaction was quenched with ice water and saturated NH4Cl followed by EtOAc. The aqueous layer was extracted with EtOAc. The combined organics were concentrated and purified by silica column (25-30% EtOAc/hexanes) chromatography to yield bis(4-chlorophenyl)(4,8-dibromoquinolin-6-yl)methanol. (M+H)+: 536, 540, 541

1. dissolutionThe resulting mixture was slowly dissolved
2. customafter 30 min
3. waitDuring this period of time
4. temperaturecooling
5. customrose above room temperature
6. customthe reaction was quenched with ice water and saturated NH4Cl
7. extractionThe aqueous layer was extracted with EtOAc
8. concentrationThe combined organics were concentrated
9. custompurified by silica column (25-30% EtOAc/hexanes) chromatography