2-Bromo-9,9-dihexyl fluorene

Synthesis of 2-bromo-9, 9-dihexylfluorene; 9.8 g of 2-bromofluorene, 39.6 g 1-bromohexane, 2.58 g tetrabutylammonium bromide and 75 ml 50percent NaOH were added into a 250 ml round bottom flask. The mixture was stirred and heated to 80 9, 9- dihexylacrylamide -2 - bromofluorene at room temperature IVa, drying good 250 ml three-mouth flask, tube, three-way for a good connection, into the magneton, taking 2 - bromofluorene 1.6g (6.5mmol), adding DMSO 35 ml, vacuum through argon, repeated 3 times. To join the bromo-hexane 2 ml (14mmol) with a benzyl triethyl ammonium chloride 73 mg (20mmol) add 10 ml 50percent NaOH (NaOH 7.58g), in NTo a 250 mL three-neck flask, compound 1 (20 g, 80 mmol) was added, Tetrabutylammonium bromide (1.315 g, 4.1 mmol), 50percent NaOH, 8 mL, 50 mL of DMSO, after stirring for half an hour at room temperature, bromohexane was added(29.618g, 179.5mmol), turn on the stirrer and heat up to 45°C, Reaction 8h. After the reaction was completed, multiple extractions with petroleum ether and deionized water were performed.The upper organic layer was dried over anhydrous magnesium sulfate and purified by column chromatography (eluent:Ethyl acetate: petroleum ether = 1:20). Get a transparent oily liquid, Compound 2 is obtained after vacuum drying, ie2-bromo-9, 9-dihexylhydrazine(30.1g, The yield is 89percent).To a 250mL three-vial bottle, In order to add compound 1 (ie 2-bromofluorene)20 g (80 mmol) of tetrabutylammonium bromide 1.315 g (4.1 mmol)And mass fraction 50percent NaOH solution 8mL, Inject 50mL of dimethyl sulfoxide (DMSO) again.After stirring for half an hour at 25°C, Bromohexane (29.618 g, 179.5 mmol) was added dropwise.Turn on the stirrer to raise the temperature to 45°C and react for 8 hours.After the reaction was completed, multiple extractions were performed with ethyl acetate and deionized water, and the upper organic layer was dried over anhydrous magnesium sulfate.The solvent was distilled off under reduced pressure, and then subjected to silica gel column chromatography with ethyl acetate/petroleum ether (1:20) as eluent to obtain a transparent oily liquid.Compound 2, 2-bromo-9, 9-dihexyl-tetrazole, After vacuum drying, 30.1 g (89percent) was obtained.step 1, Add Compound 1 (5g, 20mmol) to a 100mL three-necked flask, Tetrabutylammonium bromide (0.3287 g, 1.025 mmol), 50percent NaOH 2mL, DMSO 12mL, After stirring at room temperature for half an hour, Add bromohexane (7.404 g, 44.87 mmol), Turn on the stirrer and warm it up to 45 °C.Reaction for 8 h.After the reaction is over, Extracted several times with petroleum ether and deionized water, The upper organic layer was dried over anhydrous magnesium sulfate.Purification by column chromatography (eluent: ethyl acetate: petroleum ether = 1:20).Obtaining a clear oily liquid, After drying in vacuo, compound 2 is obtained.That is, 2-bromo-9, 9-dihexylfluorene (7.525 g, yield 89percent).2-Bromofluorene (1 g, 4.1 mmol) was dissolved in DMF (N, N-dimethylformamide) (6 mL). Potassium tert-butoxide (C4H9KO) was added and the solution was dark red. After the mixture was stirred at room temperature for 15 minutes, 1-bromo-n-hexane (1.44 mL, 1.68 g, 10.2 mmol) was added dropwise, and the color of the solution changed from dark red to grayish green. Stirring reaction mixture at 60 ° CThe mixture was left overnight (12 hours) until the mixture was gray. It was cooled to room temperature, and extracted with water and diethyl ether. Using silica gel powder as a stationary phase and n-hexane as an eluent, 1.24 g of a pale yellow oily liquid (yield: 73percent) was obtained by column chromatography. The reaction equation is as follows:

Molecular Weight:413.4
XLogP3:10.5
Rotatable Bond Count:10
Exact Mass:412.17656
Monoisotopic Mass:412.17656
Heavy Atom Count:26
Complexity:391
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes