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CAS No. : | 2523-37-7 | MDL No. : | MFCD00126475 |
Formula : | C14H12 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZVEJRZRAUYJYCO-UHFFFAOYSA-N |
M.W : | 180.25 | Pubchem ID : | 17299 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal at 475 - 480℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With lithium aluminium tetrahydride; oxygen In tetrahydrofuran at 0℃; for 2.5h; Reflux; | |
With pyridine; benzene-trimethyl-ammonium hydroxide; oxygen | ||
With sodium hydroxide; potassium permanganate |
Stage #1: 9-methylfluorene With triethylsilane; oxygen In acetonitrile for 1h; Irradiation; Stage #2: With triphenylphosphine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With soda lime durch Destillation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; | |
90% | With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; | |
76% | Stage #1: 9-methyl-9H-fluoren-9-ol In acetic acid Heating; Stage #2: With hydrogen In acetic acid at 20℃; Further stages.; |
74% | Stage #1: 9-methyl-9H-fluoren-9-ol With acetic acid Reflux; Stage #2: With hydrogen | 7 The synthesis of 4 starts from commercially available 9-fluorenone, which is methylated using MeMgl forming 26. This compound was then converted into 9-methyl-9W-fluorene by acid catalyzed dehydration in refluxing glacial acetic acid followed by overnight reduction using Pd/C and H2 (1 atm - balloon) in a one pot procedure. 9-Methyl-9W-fluorene was obtained in a 67% yield (2 steps) starting from 20 grams of 9-fluorenone ( 111 mmol). 9-Methyl-9AY-fiuorene was subsequently used to capture gaseous C02 after deprotonation using n-BuLi in cold THF. Using excess C02 resulted in a total isolated yield of 91% of the acid precursor 27 after recrystallization . 9-Methyl-9H- fluorene was also used for the capture of [13C]-C02 applied as limiting reagent, resulting in a 73% isolated yield of *27. 27 and *27 was then transformed quantitatively into their acid chloride derivatives 4 and *4 using oxalyl chloride and a ca DMF in CH2CI2 at 30 °C. |
70% | With hydrogen In acetic acid for 1h; Heating; | |
45% | With H | |
With hydrogen iodide; acetic acid | ||
With acetic acid anschliessende Hydrierung an Platin; | ||
88 % Spectr. | With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran for 24h; ultrasonic irradiation; | |
With zinc In acetic acid | ||
With iodine; hypophosphorous acid In acetic acid | ||
With triethylsilane; diethyl ether; boron trifluoride | ||
Multi-step reaction with 2 steps 1: aluminium phosphate / 250 °C / im Vakuum 2: palladium black; diethyl ether / Hydrogenation | ||
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h; | ||
Multi-step reaction with 2 steps 1: acetic acid / Reflux 2: palladium on carbon; hydrogen / 760.05 Torr | ||
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 6% 2: 10% 3: 55% | In water Irradiation; | |
1: 55% 2: 6% 3: 10% | In water Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1.5h; Stage #2: methyl iodide In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.; | |
99% | With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | |
91.9% | Stage #1: 9H-fluorene With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 20℃; Inert atmosphere; | 9-Methylfluorene. To fluorene (13.5 g, 81.3mmol) dissolved in THF (75 ml), the lithium diisopropylamide (LDA) (41 ml) was dropwise added at -10 oC under N2, and the mixture wasstirred for 1 h. Then, iodomethane (5 ml) was added into the reaction in oneportion. The solution was then stirred overnight at room temperature. Then, thereaction mixture was poured into water and acidified to pH = 2-3 with 1 Mhydrochloric acid. The resulting mixture was extracted with ethyl acetate. Thecombined organic phase was washed with brine and dried over anhydrous MgSO4.After filtering, the solvent was removed in vacuum and the resulting crudeproduct was purified by column chromatography (silica, hexane) to yield a whitesolid (13.45 g, 91.9 %). |
91% | Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; for 1.75h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In tetrahydrofuran; hexane at -60 - 20℃; for 2.33333h; Inert atmosphere; Schlenk technique; | |
88% | With n-butyllithium In tetrahydrofuran | |
75% | Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; | |
50% | Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; | |
With n-butyllithium 1.) hexane, THF, -78 deg C, 30 min, 2.) hexane, THF, a) -78 deg C, 30 min, b) RT, overnight; Yield given. Multistep reaction; | ||
With n-butyllithium 1.) THF, -78 deg C, 45 min.; up to room temp., 1 h., 2.) -78 deg C, 45 min., THF,; up to room temp., 12 h.; Yield given. Multistep reaction; | ||
Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 0.25h; Further stages.; | ||
With n-butyllithium; sodium chloride In tetrahydrofuran; hexane; ethyl acetate | 5 2-(Bromoacetyl)-9-methylfluorene PREPARATION 5 2-(Bromoacetyl)-9-methylfluorene To a solution of 30 g. of fluorene in 500 ml. of anhydrous tetrahydrofuran cooled to -78° C. by means of an external dry ice/acetone bath were added 120.5 ml. of a 1.6 M solution of n-butyl lithium in hexane. After stirring for 30 minutes, the reaction mixture was added to a -78° C. solution of 56.2 ml. of methyl iodide in 60 ml. of anhydrous tetrahydrofuran. The reaction was stirred for 30 minutes at -78° C. and then overnight at room temperature. The tetrahydrofuran was removed by evaporation and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with water followed by a saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated to dryness. Recrystallization from methanol provided 26.5 g. of 9-methylfluorene, m.p. 44°-45° C. | |
85 %Chromat. | With lithium diisopropyl amide In tetrahydrofuran at -10℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 3% 2: 8% 3: 13% 4: 10% | In acetonitrile for 14h; Ambient temperature; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 8% 2: 19% 3: 13% 4: 3% | With acridine In acetonitrile for 14h; Ambient temperature; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 475 - 480℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 9-methylfluorene With triethylsilane; [Bu4N]4W10O32; oxygen In acetonitrile at 5 - 10℃; for 1h; Irradiation; Stage #2: With triphenylphosphine Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) Mg / 1.) Et2O, 2.) Et2O 2: 1.) NaH / 1.) THF, 2.) THF, 0 deg C to 25 deg C 3: 10 percent / C6H5SH / various solvent(s) / 1 h / 180 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1% Au/TiO2 In ethyl acetate at 55℃; for 1h; Overall yield = 96 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium hydride In dimethyl sulfoxide at 60℃; for 6h; Inert atmosphere; | To 9-methylfluorene (3.6 g, 20 mmol) in dry DMSO (40 mL), NaH (60%, 0.48 g, 20 mmol) wasadded slowly in a N2 atmosphere. Then, diethyl (2-bromoethyl)phosphonate(5.0 g, 20.4 mmol) was addedinto the reaction, and then mixture was heated at 60 oC for 6 h. Theresulted mixture was poured into water (50 mL), which was extracted with ethylacetate (3×40 mL). The organic phase was washed with brine, and dried withmagnesium sulfate and the solvent was removed under vacuum. The residue wasdissolved in a minimum amount of ethyl acetate and chromatographic separationon silica was achieved by eluting with pet. ether:ethyl acetate (2:1). Thesolvent was removed under reduced pressure to give(2-(9-methyl-9H-fluoren-9-yl)ethyl)phosphonate as pale yellow liquid (5 g, 75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 56% 2: 47% | With lithium aluminium tetrahydride In tetrahydrofuran at 4℃; for 3h; Reflux; |