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[ CAS No. 486-52-2 ]

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2D
Chemical Structure| 486-52-2
Chemical Structure| 486-52-2
Structure of 486-52-2 *Storage: {[proInfo.prStorage]}

Quality Control of [ 486-52-2 ]

Related Doc. of [ 486-52-2 ]

SDS

Product Details of [ 486-52-2 ]

CAS No. :486-52-2MDL No. :N/A
Formula : C20H14 Boiling Point : -
Linear Structure Formula :-InChI Key :QBBPWJMJLXOORS-UHFFFAOYSA-N
M.W :254.33Pubchem ID :15559295
Synonyms :

Computed Properties of [ 486-52-2 ]

TPSA : 0 H-Bond Acceptor Count : 0
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.10 Rotatable Bond Count : 0

Safety of [ 486-52-2 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 486-52-2 ]

  • Downstream synthetic route of [ 486-52-2 ]

[ 486-52-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 486-52-2 ]
  • [ 848982-57-0 ]
  • 2
  • [ 486-52-2 ]
  • CH3OCH2CH2-halide [ No CAS ]
  • [ 204265-32-7 ]
  • 5
  • [ 74-83-9 ]
  • [ 486-52-2 ]
  • [ 872705-63-0 ]
YieldReaction ConditionsOperation in experiment
84.5% With tetrabutylammomium bromide; In toluene;Reflux; Add 150 mL of toluene to the reactor.Intermediate 7-2 (12.72 g, 50 mmol),Methyl bromide (27.7 g, 292 mmol),Tetrabutylammonium bromide (1.37 g, 4.25 mmol) was refluxed,cool down,Column chromatography gave Intermediate 7-3 (13.12 g, 84.5%).
84.5% With tetrabutylammomium bromide; In toluene;Reflux; 150 mL of toluene was added to the reactor, Intermediate 17-2 (12.72g, 50mmol), methylene bromide (27.7g, 292mmol), tetrabutylammonium bromide (1.37g, 4.25mmol), were added and refluxed, cooled, column chromatography to give intermediate 17-3 (13.12 g, 84.5%).
84.5% With tetrabutylammomium bromide; In toluene;Reflux; 150 mL of toluene, Intermediate 6-2 (12.72 g, 50 mmol), methyl bromide (27.7 g, 292 mmol), and tetrabutylammonium bromide (1.37 g, 4.25 mmol) were refluxed, cooled, and subjected to column chromatography. Intermediate 6-3 (13.12 g, 84.5%).
84.5% With tetrabutylammomium bromide; In toluene;Reflux; Step 3: 150 mL of toluene, Intermediate 2-2 (12.72 g, 50 mmol) were added to the reactor.Methyl bromide (27.7 g, 292 mmol) and tetrabutylammonium bromide (1.37 g, 4.25 mmol) were refluxed.Cooling and column chromatography gave Intermediate 2-3 (13.12 g, 84.5%).
14.76 g With tetrabutylammomium bromide; In toluene;Reflux; Add 1-1 (31.81 g, 100.00 mmol) to 50.0 mL of concentrated sulfuric acid,Stir at room temperature for 2 h,It was found that the color of the reaction solution turned yellow.Slowly add 300.0mL of water,Neutralize the reaction solution with sodium hydroxide to neutrality,There is solid precipitation,After cooling, suction filtration gave 1-2 (21.18 g, 75.56 mmol).Dissolve 1-2 in 150 ml of ethylene glycol,Add 40 ml of 30% hydrazine hydrate reflux reaction.The reaction solution is cooled and poured into water.The precipitate was filtered to give a white solid 1-3 (14.29 g, 56.12 mmol).Dissolve 1-3 in 150 mL of toluene,Add 30g 1-4,1.5 g of tetrabutylammonium bromide,Reflux,Cooling filter column chromatography to obtain white powder(14.76 g, 47.55 mmol).Finally, it will be brominated,The white powder was dissolved in 100.0 mL of chloroform.Add 1.0g of anhydrous ferric chloride,20.0 mL of liquid bromine was added dropwise at zero, and the reaction was completed. The reaction solution was washed with a saturated solution of sodium sulfite and spun dry.A white solid intermediate A was obtained.Suggest an edit
14.76 g With tetrabutylammomium bromide; In toluene; for 2h;Reflux; Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol).1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol).1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, it will be brominated,The white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After completion of the reaction, the reaction solution was washed with a saturated solution of sodium sulfite and dried to give a white solid (18.83). g, 40.22 mmol).
14.76 g With tetrabutylammomium bromide; In toluene;Reflux; The 2 - 1 (31.81 g, 100 . 00 mmol) adding 50.0 ml concentrated sulfuric acid, stirring at the room temperature 2 h, found that the color yellow reaction solution, slowly adding 300.0 ml water, sodium hydroxide and the reaction to reserve in neutral, solids are separated out, after cooling filtered to get solid 1 - 2 (21.18 g, 75 . 56 mmol). The 2 - 2 dissolved in 150 ml ethylene glycol, by adding 40 ml 30% hydrazine hydrate reflux reaction, but the reaction is poured into the water in the after cooling, filtration and precipitation to obtain white solid 2 - 3 (14.29 g, 56 . 12 mmol). The 1 - 3 is dissolved in 150 ml in toluene, adding 30 g 2 - 4, 1.5 g [...] bromination amine, reflux, cooling filtration column chromatography to obtain white powder (14.76 g, 47 . 55 mmol). Finally its bromo, the white powder dissolved in 100.0 ml in chloroform, adding 1.0 g anhydrous ferric chloride, zero dropwise 20.0 ml bromine, the reaction is completed, a sodium sulfite saturated solution many times reaction solution, turns on lathe does, to obtain white solid (18.83 g, 40 . 22 mmol).
14.76 g With tetrabutylammomium bromide; In toluene;Reflux; Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol). 1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol). 1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, the bromination, the white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After the reaction was completed, the reaction solution was washed with a saturated solution of sodium sulfite, and dried. A white solid intermediate A (18.83 g, 40.22 mmol) was obtained
14.76 g With tetrabutylammomium bromide; In toluene;Reflux; Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol). 1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol). 1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, the bromination, the white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After the reaction was completed, the reaction solution was washed with a saturated solution of sodium sulfite, and dried. A white solid intermediate A (18.83 g, 40.22 mmol) was obtained.

  • 6
  • [ 5695-13-6 ]
  • [ 486-52-2 ]
YieldReaction ConditionsOperation in experiment
92% With hydrazine hydrate; In 1,2-dimethoxyethane;Reflux; Add intermediate 7-1 (16.94 g, 60 mmol) to the reactor.Ethylene glycol 150mL,40mL of 30% hydrazine hydrate,After the reflux reaction is completed,The reaction solution is cooled and poured into water.Filtration gave Intermediate 7-2 (14.04 g, 92%).
92% With hydrazine hydrate; In ethylene glycol;Reflux; Intermediate 17-1 (16.94g, 60mmol), ethylene glycol 150mL, 40mL 30% hydrazine hydrate were added to the reactor. After the reflux reaction was completed, the reaction solution was cooled, poured into water, and filtered to obtain Intermediate 17-2 (14.04 g, 92%).
92% With hydrazine hydrate; In 1,2-dimethoxyethane;Reflux; Intermediate 6-1 (16.94g, 60mmol), ethylene glycol 150mL, 40mL 30% hydrazine hydrate were added to the reactor. After the reflux reaction was completed, the reaction solution was cooled, poured into water, and filtered to obtain Intermediate 6-2 (14.04 g, 92%).
92% With hydrazine hydrate; In ethylene glycol;Reflux; Step 2: Intermediate 2-1 (16.94 g, 60 mmol), ethylene glycol 150 mL, and 40 mL of 30% hydrazine hydrate were added to the reactor. After the reflux reaction was completed,The reaction solution was cooled, poured into water and filtered to afford Intermediate 2-2 (14.04 g, 92%).
50% With hydrazine; In diethylene glycol; at 200℃; for 2h; Ten gram (0.035 mol) of Intermediate 2, 8.8 mL (0.175 mol) of hydrazine monohydrate, and 300 mL of diethylene glycol were added to a 1-L flask, and the whole was stirred under heat at 200C for 2 hours. After the completion of the reaction, water was added to the resultant, and the precipitate was separated by filtration. The coarse reaction product was reprecipitated with hexane and chloroform, whereby 4.5 g of Intermediate 3 (tan solid, 50% yield) as a target were obtained.
50% With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 200℃; for 2h; (1-3) Synthesis of Intermediate 3; Into a 1 liter flask, 10 g (0.035 moles) of Intermediate 2, 8.8 ml (0.175 moles) of hydrazine monohydrate, 12 g (0.18 moles) of potassium hydroxide and 300 ml of diethylene glycol were placed, and the obtained mixture was heated at 200 C. for 2 hours under stirring. After the reaction was completed, water was added, and the formed precipitates were separated by filtration. The crude reaction product was reprecipitated from hexane:chloroform, and 4.5 g of Intermediate 3 of the object compound was obtained (a light brown solid substance; the yield: 50%).
50% With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 160 - 196℃; for 48h; In a 250 mL three-necked round bottom flask was added indenofluorenidione1.5 g (5.3 mmol),120 mLDiethylene glycol,Then add 7.5 g of KOH and 8 mL of 98% hydrazine monohydrateThe Then install a thermometer and a reflux condenser on a round bottom flask The temperature of the mixture is heated to 160 C, the temperature can not continue to rise, the heating reflux 24 h, the device is changed to a distillation device, the water generated in the reaction and the excess hydrazine hydrate are removed by distillation, and then the temperature is raised, The temperature was raised to 196 C and heated to reflux for 24 h. After the completion of the reaction, the hot reaction solution was poured into ice water mixed with dilute hydrochloric acid In the material, there are solid solids, standing for a while, the Buchner funnel filter the resulting gray solid, washed several times with water, and then the resulting solid Was added to glacial acetic acid to recrystallize, and finally a white solid indenofluorene 2a was obtained in 50% yield.
50% With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 160 - 196℃; for 48h; In a 250 mL three-necked round bottom flask, 1.5 g (5.3 mmol) of indenovluidinedione and 120 mL of diethylene glycol were added followed by 7.5 g of KOH and 8 mL of 98% hydrazine monohydrate and a thermometer And the reflux condenser was heated slowly to the temperature of the mixture at 160 C. The temperature was unable to continue to rise. After heating for 24 hours, the apparatus was changed to a distillation apparatus, and the water generated in the reaction was distilled off. The amount of hydrazine hydrate, and then continue to heat up, the temperature rose to 196 C heating reflux reaction 24 h, after the end of the reaction of the hot reaction solution into dilute hydrochloric acid containing ice water mixture, solid production, standing for a while, The resulting solid was filtered through water and washed several times with water. The resulting solid was then recrystallized from glacial acetic acid and finally a white solid indenofluorene 2a was obtained in 50% yield.
50% With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 160 - 196℃; for 48h; The indenyl fluorenone was added to a 250 mL three-necked round bottom flask1.5 g (5.3 mmol),120 mL diethylene glycol,Then add 7.5 g of KOH and 8 mL of 98% hydrazine monohydrate.The thermometer and the reflux condenser were then placed on a round bottom flask,The temperature of the mixture is heated to 160 C and the temperature can not continue to rise,After heating for 24 h,The device is changed to a distillation unit,The water generated in the reaction and the excess hydrazine hydrate were distilled off,And then continue to heat up, the temperature rose to 196 C heating reflux reaction 24 h,After the completion of the reaction, the hot reaction solution was poured into ice water mixed with dilute hydrochloric acidIn the material, there are solid solids, standing for a while, the Buchner funnel filter the resulting gray solid, washed several times with water, and then the resulting solidWas added to glacial acetic acid to recrystallize, and finally a white solid indenofluorene 2a was obtained in 50% yield.
With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 220℃; for 48h; Preparation of Compound (221); Compound (220) (12.0 g, 43.0 mmol) obtained as above was dissolved in diethylene glycol (140 mL), and potassium hydroxide (24.0 g, 425.0 mmol) and hydrazine hydrate (20.7 mL, 430 mmol) were added thereto. After stirring at 220 C. for 48 hours, the reaction mixture was cooled to 25 C., and 20% hydrochloric acid solution (400 mL) was added thereto. After stirring for 1 hour, the solid produced was filtered under reduced pressure. Acetone and tetrahydrofuran (200 mL each) were added to the solid, and the mixture was stirred for 20 hours, filtered under reduced pressure and dried under reduced pressure to obtain Compound (221) named as indenofluorene (8.5 g, 33.4 mmol).
14.29 g With hydrazine hydrate; In ethylene glycol;Reflux; Add 1-1 (31.81 g, 100.00 mmol) to 50.0 mL of concentrated sulfuric acid,Stir at room temperature for 2 h,It was found that the color of the reaction solution turned yellow.Slowly add 300.0mL of water,Neutralize the reaction solution with sodium hydroxide to neutrality,There is solid precipitation,After cooling, suction filtration gave 1-2 (21.18 g, 75.56 mmol).Dissolve 1-2 in 150 ml of ethylene glycol,Add 40 ml of 30% hydrazine hydrate reflux reaction.The reaction solution is cooled and poured into water.The precipitate was filtered to give a white solid 1-3 (14.29 g, 56.12 mmol).Dissolve 1-3 in 150 mL of toluene,Add 30g 1-4,1.5 g of tetrabutylammonium bromide,Reflux,Cooling filter column chromatography to obtain white powder(14.76 g, 47.55 mmol).Finally, it will be brominated,The white powder was dissolved in 100.0 mL of chloroform.Add 1.0g of anhydrous ferric chloride,20.0 mL of liquid bromine was added dropwise at zero, and the reaction was completed. The reaction solution was washed with a saturated solution of sodium sulfite and spun dry.A white solid intermediate A was obtained.Suggest an edit
14.29 g With hydrazine hydrate; In ethylene glycol;Reflux; Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol).1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol).1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, it will be brominated,The white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After completion of the reaction, the reaction solution was washed with a saturated solution of sodium sulfite and dried to give a white solid (18.83). g, 40.22 mmol).
14.29 g With hydrazine hydrate; In 1,2-dimethoxyethane;Reflux; The 2 - 1 (31.81 g, 100 . 00 mmol) adding 50.0 ml concentrated sulfuric acid, stirring at the room temperature 2 h, found that the color yellow reaction solution, slowly adding 300.0 ml water, sodium hydroxide and the reaction to reserve in neutral, solids are separated out, after cooling filtered to get solid 1 - 2 (21.18 g, 75 . 56 mmol). The 2 - 2 dissolved in 150 ml ethylene glycol, by adding 40 ml 30% hydrazine hydrate reflux reaction, but the reaction is poured into the water in the after cooling, filtration and precipitation to obtain white solid 2 - 3 (14.29 g, 56 . 12 mmol). The 1 - 3 is dissolved in 150 ml in toluene, adding 30 g 2 - 4, 1.5 g [...] bromination amine, reflux, cooling filtration column chromatography to obtain white powder (14.76 g, 47 . 55 mmol). Finally its bromo, the white powder dissolved in 100.0 ml in chloroform, adding 1.0 g anhydrous ferric chloride, zero dropwise 20.0 ml bromine, the reaction is completed, a sodium sulfite saturated solution many times reaction solution, turns on lathe does, to obtain white solid (18.83 g, 40 . 22 mmol).
14.29 g With hydrazine hydrate; In diethylene glycol;Reflux; Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol). 1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol). 1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, the bromination, the white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After the reaction was completed, the reaction solution was washed with a saturated solution of sodium sulfite, and dried. A white solid intermediate A (18.83 g, 40.22 mmol) was obtained
14.29 g With hydrazine hydrate; In ethylene glycol;Reflux; Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol). 1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol). 1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, the bromination, the white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After the reaction was completed, the reaction solution was washed with a saturated solution of sodium sulfite, and dried. A white solid intermediate A (18.83 g, 40.22 mmol) was obtained.

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  • 7
  • [ 486-52-2 ]
  • 6,6'-(6,6,12,12-tetrabutyl-6,12-dihydroindeno[1,2b]fluorene-2,8-diyl)bis(2,2-difluoro-4-methyl-2H-1,3,2-dioxaborinin-1-ium-2-uide) [ No CAS ]
  • 8
  • [ 486-52-2 ]
  • 1,1'-(6,6,12,12-tetrabutyl-6,12-dihydroindeno[1,2b]fluorene-2,8-diyl)diethanone [ No CAS ]
  • 9
  • [ 486-52-2 ]
  • [ 117184-75-5 ]
  • C56H68As2 [ No CAS ]
  • 10
  • [ 109-65-9 ]
  • [ 486-52-2 ]
  • [ 1126881-22-8 ]
YieldReaction ConditionsOperation in experiment
Under nitrogen protection,To the baked dried shrek bottle was added indenofluorene (2.54 g, 10.0 mmol)And 100 mL of the treated anhydrous THF, sealed the reaction flask, nitrogen atmosphere,Place the reaction bottle at a temperature that has cooled to -20 CHydrazine,After cooling for half an hour, 12 mL of n-butyllithium n-BuLi solution (2.5 M) was added dropwise over half an hour using a syringesolution n-hexane, 30.0 mmol). After completion of the dropwise addition, the reaction flask was taken out and the magnetic stirrer was allowed to stand for half an hour at room temperature. Then, the reaction flask was placed in minus 20 degrees Celsius cold hydrazine bath,After half an hour, add 3.2 mL of n-bromobutane dropwise with a syringe over 10 min. After a while, the reaction flask was removed and stirred at room temperature for 4 h.Then repeat the above process,Add 12 mL n-BuLi at -20 C, respectively(2.5 M solution n-hexane, 30.0 mmol)And 3.2 mL of n-bromobutane were added, and the mixture was stirred at room temperature for 12 h,TLC plate to monitor the reaction process, the reaction is complete, adding saturated chlorinationAmmonium solution to quench the reaction, the mixture into the separatory funnel, add petroleum ether extraction, standing stratification, collecting the upper organicLayer, extracted three times, in the collected organic phase by adding anhydrous magnesium sulfate drying 2 h, filter out the anhydrous magnesium sulfate, in the vacuumThe pump was concentrated by evaporation, the residue was dissolved in methylene chloride and adsorbed on silica gel. The samples were dried and the petroleum ether was used as the eluent,And separated by silica gel chromatography to give a white solid 2b.
Under a nitrogen atmosphere, indene fluorene (2.54 g, 10.0 mmol) and 100 mL of the treated anhydrous tetrahydrofuran were added to the baked dried shrek bottle and the reaction flask was sealed. The reaction flask was placed at a temperature has been reduced to -20C in cold hydrazine and after cooling for half an hour, add 12 mL of 2.5 M n-butyllithium n-hexane solution (2.5 Mu solution n-hexane, 30 0 mmol), after completion of the drop, the reaction bottle after a moment, in the temperature under the conditions of magnetic stirring for half an hour, then the reaction bottle into minus 20 degrees Celsius cold hydrazine bath, half an hour later, with a syringe in 10min (4.1 g, 30.0 mmol) was added dropwise. After a few minutes, the reaction flask was taken out and stirred at room temperature for 4 h. The procedure was repeated by adding 12 11112 / (0.1111-hexane, 30.0 mmol) and 3.2 mL of n-bromobutane were added. After the dropwise addition, the reaction was carried out at room temperature for 12 h. The TLC plate was used to monitor the reaction. After the reaction was complete, Ammonium chloride solution to quench the reaction, the mixture into the separatory funnel, add petroleum ether extraction, The layers were collected and the organic layer was collected. After three times, the organic phase was collected and dried over anhydrous magnesium sulfate for 2 h. The anhydrous magnesium sulfate was removed by suction filtration, evaporated on a vacuum chestnut and the residue was dissolved in dichloromethane After adsorption on silica gel, dry on the sample, with petroleum ether as eluent, silica gel chromatography column separation, can be white solid 2b.
Under nitrogen protection,In a baked dried schlenk bottle, indenofluorene (2.54 g, 10.0 mmol) and 100 mLThe treated anhydrous THF,Sealed reaction bottle,Under a nitrogen atmosphere,The reaction flask was placed in cold hydrazine which had been lowered to -20 C,After cooling for half an hour,A 12 mL n-butyllithium n-BuLi solution (2.5 M solution n-hexane, 30.0 mmol) was added dropwise over half an hour using a syringe,After the drop is completed, the reaction bottle is removed after a moment,At room temperature under the conditions of magnetic stirring for half an hour, then the reaction bottle into minus 20 degrees Celsius cold hydrazine bath,Half an hour later,With a syringe in 10 min dropwise add 3.2 mL of n-bromobutane,After a while, the reaction flask was removed and stirred at room temperature for 4 h. Then repeat the above process, ie12 mL n-BuLi (2.5 M solution n-hexane, 30.0 mmol) and 3.2 mL n-bromide were added at -20 CButane was added, and the mixture was stirred at room temperature for 12 h. The TLC plate was used to monitor the reaction process. After the reaction was complete, saturated chlorinationAmmonium solution to quench the reaction, the mixture into the separatory funnel, adding petroleum ether extraction, standing stratification, collecting the upper organicLayer, extracted three times, in the collected organic phase by adding anhydrous magnesium sulfate drying 2 h, filter out the anhydrous magnesium sulfate, in the vacuumThe pump was concentrated by evaporation, the residue was dissolved in methylene chloride and adsorbed on silica gel. The sample was dried and the petroleum ether was used as the eluent,And separated by silica gel chromatography to give a white solid 2b.
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