反应详情

温度

-15 °C

A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with i-PrMgCl.LiCl (1 mL, 1.05 M in THF, 1.05 mmole), the reaction mixture was cooled to −15° C. and 1,2-dibromobenzene (235.9 mg, 1 mmole) was then added dropwise. The Br/Mg-exchange was complete after 1.5 h (checked by GC analysis of reaction aliquots, conversion more than 98%) and solution of CuCN.2LiCl (0.1 mL, 1.0 M in THF, 0.1 mmole) was added. After stirring for 10 min at −15° C. benzoyl chloride (140.6 mg, 1 mmole) was added. The reaction mixture was stirred for 1 h at −15° C. and was then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3 was added. The aqueous phase was extracted with ether (3×4 mL) and the organic fractions were washed with brine (5 mL), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (dichloromethane) yielding the ketone (2ka) as a white cristals (219.3 mg, 84%). 1H-NMR (CDCl3, 200 MHz): δ=7.86-7.78 (m, 2H); 7.68-7.56 (m, 2H); 7.52-7.30 (m, 5H).

1. customA dry
2. customargon flushed 10 mL flask
3. customequipped with a magnetic stirrer
4. additiona septum, was charged with i-PrMgCl
5. additionwas added
6. customwas then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3
7. additionwas added
8. extractionThe aqueous phase was extracted with ether (3×4 mL)
9. washthe organic fractions were washed with brine (5 mL)
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated in vacuo
12. customThe crude residue was purified by flash chromatography (dichloromethane)