反应详情

温度

2.5 °C

To a solution of 2,7-dibromo-9-(bis-methylsulfanyl-methylene)fluorene (4.28, 10 mmol) in dry THF (70 ml) at 0° C. under nitrogen, was added a solution of lithium tetrachlorocuprate (2 ml of a 0.1M solution in THF, 2 mol %). A solution of dodecylmagnesium bromide (22 ml of a 1.0M solution in diethyl ether, 0.022 mol) was added dropwise over 15 min. The reaction was stirred for 3 h at 0-5° C. before quenching with 5% NaOH (100 ml). The reaction was stirred for 10 min and then filtered through celite. The organic layer was separated and the aqueous layer further washed with ethyl acetate (100 ml). The combined organics were washed with brine (100 ml), dried (sodium sulfate), and concentrated under reduced pressure. The crude oil was further purified by filtration through a plug of silica (5 cm×5 cm) covered with a layer of basic alumina (1 cm×5 cm), eluting with petrol. After concentration the residue was recrystallized from isohexane to afford 4.2 of the product as white crystals (62%). Purity (HPLC>98%). 1H and 13C NMR spectra as expected.

1. custombefore quenching with 5% NaOH (100 ml)
2. stirringThe reaction was stirred for 10 min
3. filtrationfiltered through celite
4. customThe organic layer was separated
5. washthe aqueous layer further washed with ethyl acetate (100 ml)
6. washThe combined organics were washed with brine (100 ml)
7. dry with materialdried (sodium sulfate)
8. concentrationconcentrated under reduced pressure
9. filtrationThe crude oil was further purified by filtration through a plug of silica (5 cm×5 cm)
10. washeluting with petrol
11. concentrationAfter concentration the residue
12. customwas recrystallized from isohexane