2-Bromo-9,9-diethylfluorene

To a solution of 2-bromofluorene (2.5 g, 10 mmol) in toluene (40 ml) was added tetrabutylammonium bromide (0. [8] g, 2.48 mmol) as a phase transfer catalyst. A freshly prepared solution of aqueous sodium hydroxide (25 ml, 50percent w/w) was added at once to the solution. The mixture turned orange and became viscous. To this solution, [IODOETL1ANE] (2.4 ml, 30 mmol) was added. The mixture was stirred at [60 °C] for a period of 8 h. It was diluted with ethyl acetate (25 ml) and washed several portions of water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product liquid. The products were purified by column chromatography (silica gel, hexane as eluent, [RF=] 0.8 on thin layer chromatography) giving colorless oil [OF 2-BROMO-9, ] 9-diethylfluorene (2.5 g) in a yield of 82percent. [IH] NMR [(CDCL3)] [S0.] 24 (t, J = 8 Hz, 6H), 1.94-1. 91 (m, 4H), 7.25-7. 23 (m, 3H), 7.38-7. 36 (m, 2H), 7.49-7. 46 (m, 1H), and 7.61-7. 59 (m, 1H).Under an argon atmosphere, the 5.0g2- bromofluorene was dissolved in 10mL dimethylsulfoxide (DMSO), and then was added 0.26g of tetrabutylammonium bromide (TBABr), was added 10mL freshly prepared solution of sodium hydroxide (hydrogen sodium oxide to water mass ratio of 1: 1), after mixing, was added 4.8mL dibromoethane, for 8 hours at 75 .After completion of the reaction, cooled to room temperature, extracted with ethyl acetate, separated, the organic phase was washed three times with plenty, dried over anhydrous magnesium sulfate, the organic phase was filtered, spin dry by silica gel column chromatography with petroleum ether as eluant separation, and dried to give 5.7 g of a solid, in 93percent yield.The 2-bromofluorenone (300 mg, 1 . 22mmol) dissolved in 20 ml in dimethyl sulfoxide solution, then adding potassium hydroxide, rapid stirring 30 min, a solution of red ink, slowly adding after bromo-ethane, solution gradually became purple-red, thin-layer chromatography tracking to the reaction is complete. The solution obtained is extracted with ethyl acetate, the organic layer three times washing with water, saturated NaCl solution to a washing, drying by anhydrous sodium sulfate, reducing pressure and evaporating the solvent. The crude product with pure petroleum ether column, to obtain 2-bromo -9, 9 the base fluorene-diethyl [...] (colorless oily, 335.5 mg, yield 91percent).To a stirred solution of compound 2 (4.90 g, 20.00 mmol) in DMSO (50 mL), NaOH aqueous solution (2 mL, 50percent u/u) was added. After 5 min of stirring, bromoethane (4.80 g, 44.00 mmol) was added slowly. The reaction mixture was stirred continuously for 10 h at room temperature. Then, 100 mL ethyl acetate was added into the mixture, washed with water to remove DMSO, dried over MgSO4, filtered and the solvent was removed. The residue was purified with chromatography on silica gel (eluting with petroleum ether) to get 3 (4.86 g, 16.20 mmol) as a white solid with 81percent yield. M.p. 52-53 C; 1 H NMR (CDCl3, 400 MHz), d (ppm): 0.31 (t, 6H, J 8.0 Hz), 1.99e2.04 (m, 4H), 7.33 (s, 3H), 7.46 (d, 2H, J 4.8 Hz), 7.57 (d, 1H, J 8.0 Hz), 7.66e7.68 (m, 1H).

Molecular Weight:301.2
XLogP3:6.2
Rotatable Bond Count:2
Exact Mass:300.05136
Monoisotopic Mass:300.05136
Heavy Atom Count:18
Complexity:294
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes