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[ CAS No. 66217-19-4 ] {[proInfo.proName]}

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Quality Control of [ 66217-19-4 ]

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Product Details of [ 66217-19-4 ]

CAS No. :66217-19-4 MDL No. :MFCD01568865
Formula : C12H11BrO Boiling Point : -
Linear Structure Formula :- InChI Key :FXVYIQCXQULCKL-UHFFFAOYSA-N
M.W : 251.12 Pubchem ID :236858
Synonyms :

Calculated chemistry of [ 66217-19-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.95
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.91
Log Po/w (XLOGP3) : 4.2
Log Po/w (WLOGP) : 4.0
Log Po/w (MLOGP) : 3.79
Log Po/w (SILICOS-IT) : 3.97
Consensus Log Po/w : 3.77

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.44
Solubility : 0.00913 mg/ml ; 0.0000363 mol/l
Class : Moderately soluble
Log S (Ali) : -4.1
Solubility : 0.0198 mg/ml ; 0.0000788 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.46
Solubility : 0.000867 mg/ml ; 0.00000345 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 66217-19-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 66217-19-4 ]

* 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.

  • Downstream synthetic route of [ 66217-19-4 ]

[ 66217-19-4 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 15231-91-1 ]
  • [ 74-96-4 ]
  • [ 66217-19-4 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In acetonitrile for 3h; Reflux;
98.4% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; 2.2 8.92 g (0.04 mol) of 6-bromo-2-naphthol and 150 ml of N, N-dimethylformamide were placed in a 250 ml flask and dissolved with stirring. Then, 16.58 g (0.12 mol) of anhydrous potassium carbonate During the stirring, 2.98 ml (0.04 mol) of bromoethane was added dropwise, and after the addition was completed, the temperature was raised to 100 ° C. and reacted for 1 hour.The reaction was cooled to room temperature and poured into 150mlCold water in a beaker, and add 150ml of ethyl acetate, stirred and allowed to stand, separated the organic layer, washed three times with anhydrous sulfurSodium acid drying, filtration, concentration, mixing the sample with crude silica gel, using petroleum ether as a developing agent, the silica gel column, the column liquid was evaporated to dryness solventA colorless transparent oily liquid, placed at room temperature cooling, precipitated a large number of white solid that6-bromo-2-ethoxynaphthalene9.88 g, yield 98.4%
98% With potassium carbonate In acetonitrile for 3h; Reflux;
67% With potassium carbonate; sodium iodide In acetone Reflux;
With ethanol; potassium carbonate
With sodium ethanolate; potassium iodide
With potassium carbonate In acetonitrile at 45℃; for 4h; 4.1.1.1 2-(4-((5′-Ethoxy-2′-methyl-[1,1′-biphenyl]-3-yl)methoxy)-2-fluorophenoxy)acetic acid (compound 1) General procedure: To a solution of 2a (600mg, 3.21mmol) and bromoethane (420mg, 3.85mmol) in acetonitrile was added K2CO3 (1330mg, 9.62mmol). The reaction mixture was heated to reflux with stirring for 4h. Then the reaction mixture was cooled to room temperature followed by filtration and the filtrate was concentrated under vacuum to obtain 600mg 3a (yield: 87%) as white solid.

  • 2
  • [ 15231-91-1 ]
  • [ 64-17-5 ]
  • [ 66217-19-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid at 100℃;
  • 4
  • [ 15231-91-1 ]
  • [ 64-67-5 ]
  • [ 66217-19-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate
  • 5
  • [ 32161-06-1 ]
  • [ 66217-19-4 ]
  • [ 128053-74-7 ]
YieldReaction ConditionsOperation in experiment
With magnesium Yield given;
With iodine; magnesium 1) THF, 10 min, reflux then 20 deg C, 1 h, 2) THF, 20 deg C, 2 h; Yield given. Multistep reaction;
  • 6
  • [ 66217-19-4 ]
  • [ 75-08-1 ]
  • [ 87054-04-4 ]
YieldReaction ConditionsOperation in experiment
73.5% With aluminium trichloride In neat (no solvent) at 0℃; for 1h;
  • 7
  • [ 66217-19-4 ]
  • [ 544-92-3 ]
  • [ 66217-26-3 ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper(II) sulfate In N,N-dimethyl-formamide
  • 8
  • [ 7647-01-0 ]
  • [ 64-17-5 ]
  • [ 16239-18-2 ]
  • SnCl2 [ No CAS ]
  • [ 15231-91-1 ]
  • [ 66217-19-4 ]
  • 9
  • [ 7647-01-0 ]
  • [ 64-17-5 ]
  • [ 16239-18-2 ]
  • tin [ No CAS ]
  • [ 15231-91-1 ]
  • [ 66217-19-4 ]
  • 10
  • [ 74-96-4 ]
  • [ 66217-19-4 ]
  • 6-ethoxy-[2]naphthyl magnesium (1+); bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diethyl ether
  • 11
  • [ 15231-91-1 ]
  • [ 75-03-6 ]
  • [ 66217-19-4 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydride at 20℃; for 16.5h;
60% In N,N-dimethyl-formamide 2.a a a 2-Bromo-6-ethoxy-naphthalene To a suspension of sodium hydride (800 mg, 60% oil dispersion) in DMF (20 ml) was added a solution of 6-Bromo-2-naphthol dropwise with stirring at 0°. After gas evolution had ceased, neat ethyl iodide (1.6 ml) was added dropwise to the stirred solution. The reaction was stirred overnight at rt. The reaction mixture was poured into water and extracted several times with tert-butyl methyl ether. The combined organic extracts were washed with water and brine, then dried over MgSO4, filtered and evaporated under reduced pressure to give tan solid. This was recrystallized from MeOH and dried under high vacuum to a constant wt. giving a white solid (3.11 g, 60%). 1H NMR(400 MHz, CDCl3) δ 7.92 (d, J=1.7 Hz, 1H), 7.65 (d, J=8.9 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.16 (dd, J=8.9 Hz, 2.48, 11), 7.09 (d, J=2.4 Hz, 1H), 4.15 (q, 2H), 1.49 (t, 3H).
Stage #1: 6-bromo-naphthalen-2-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: ethyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
  • 12
  • [ 66217-19-4 ]
  • [ 33513-42-7 ]
  • [ 757230-55-0 ]
YieldReaction ConditionsOperation in experiment
82% With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;
21% Stage #1: 2-ethoxy-6-bromo-naphthalene With iodine; magnesium In tetrahydrofuran for 4h; Reflux; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #3: With water; acetic acid In tetrahydrofuran
  • 13
  • [ 15231-91-1 ]
  • [ 75-00-3 ]
  • [ 66217-19-4 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3.5h;
  • 14
  • [ 66217-19-4 ]
  • [ 1692-25-7 ]
  • 3-(6-ethoxy-naphthalen-2-yl)-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 80℃;
  • 15
  • [ 66217-19-4 ]
  • 2-chloromethyl-6-ethoxy-naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 2: 79 percent / NaBH4 / methanol / 20 °C 3: SOCl2 / CH2Cl2 / 1 h / 0 °C
  • 16
  • [ 66217-19-4 ]
  • [ 757230-57-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 2: 79 percent / NaBH4 / methanol / 20 °C
  • 17
  • [ 66217-19-4 ]
  • 1-(6-ethoxy-naphthalen-2-ylmethyl)-1<i>H</i>-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 82 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 2: 79 percent / NaBH4 / methanol / 20 °C 3: SOCl2 / CH2Cl2 / 1 h / 0 °C 4: dimethylformamide / 18 h / 20 °C
  • 18
  • [ 66217-19-4 ]
  • [ 128053-75-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) Mg, I2 / 1) THF, 10 min, reflux then 20 deg C, 1 h, 2) THF, 20 deg C, 2 h 2: BBr3 / CH2Cl2 / 2.5 h / Heating
Multi-step reaction with 2 steps 1: Mg 2: BBr3 / CH2Cl2 / 3 h / 40 °C
  • 19
  • [ 66217-19-4 ]
  • [ 128053-76-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1) Mg, I2 / 1) THF, 10 min, reflux then 20 deg C, 1 h, 2) THF, 20 deg C, 2 h 2: BBr3 / CH2Cl2 / 2.5 h / Heating 3: 65 percent / NaH / dimethylformamide / 12 h / 20 °C
Multi-step reaction with 3 steps 1: Mg 2: BBr3 / CH2Cl2 / 3 h / 40 °C 3: NaH / dimethylformamide
  • 20
  • [ 66217-19-4 ]
  • [ 128053-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1) Mg, I2 / 1) THF, 10 min, reflux then 20 deg C, 1 h, 2) THF, 20 deg C, 2 h 2: BBr3 / CH2Cl2 / 2.5 h / Heating 3: 65 percent / NaH / dimethylformamide / 12 h / 20 °C 4: 81 percent / BF3*Et2O / CH2Cl2 / 20 °C
Multi-step reaction with 4 steps 1: Mg 2: BBr3 / CH2Cl2 / 3 h / 40 °C 3: NaH / dimethylformamide 4: 80 percent / BF3*OEt2 / CH2Cl2 / 144 h / 20 °C
  • 21
  • [ 66217-19-4 ]
  • [ 162968-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1) Mg, I2 / 1) THF, 10 min, reflux then 20 deg C, 1 h, 2) THF, 20 deg C, 2 h 2: BBr3 / CH2Cl2 / 2.5 h / Heating 3: 48 percent / BF3*Et2O / nitrobenzene / 5 h / 80 °C
  • 22
  • [ 66217-19-4 ]
  • [ 162968-05-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1) Mg, I2 / 1) THF, 10 min, reflux then 20 deg C, 1 h, 2) THF, 20 deg C, 2 h 2: BBr3 / CH2Cl2 / 2.5 h / Heating 3: 65 percent / NaH / dimethylformamide / 12 h / 20 °C 4: 90 percent / BF3*Et2O / CH2Cl2 / 216 h / 20 °C
  • 23
  • [ 66217-19-4 ]
  • [ 162968-06-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1) Mg, I2 / 1) THF, 10 min, reflux then 20 deg C, 1 h, 2) THF, 20 deg C, 2 h 2: BBr3 / CH2Cl2 / 2.5 h / Heating 3: 65 percent / NaH / dimethylformamide / 12 h / 20 °C 4: 90 percent / BF3*Et2O / CH2Cl2 / 216 h / 20 °C 5: 59 percent / NaH (60percent in oil), NBS / CH2Cl2; methanol / 8 h / -50 °C
  • 24
  • [ 66217-19-4 ]
  • [ 68464-16-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CuSO4, Py / dimethylformamide 2: HCl / methanol; dioxane
  • 25
  • [ 66217-19-4 ]
  • [ 33016-47-6 ]
  • [ 74-88-4 ]
  • [ 247174-69-2 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; magnesium In tetrahydrofuran; water 37.i (i) (i) Production of (6-Ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)ketone 2-Bromo-6-ethoxynaphthalene (5.3 g) was dissolved in THF (40 ml). To the solution were added magnesium (0.515 g) and methyl iodide (one drop), and the mixture was vigorously stirred to dissolve magnesium. The reaction mixture was cooled in ice bath, and a solution of 4-formyl-1-tritylimidazole (7 g) in THF (80 ml) was added dropwise over 30 min, and the mixture was stirred at room temperature for 1 h. To the reaction mixture were added saturated aqueous solution of ammonium chloride (40 ml) and water (40 ml), and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue was washed with ethyl acetate to give (6-ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)methanol (6.3 g) as a colorless powder. The product (6.3 g) was dissolved in dichloromethane (120 ml).
With ammonium chloride; magnesium In tetrahydrofuran; water R.3.i (i) (i) Production of (6-ethoxynaphthalen-2-yl) (1-trityl-1H-imidazol-4-yl)ketone 2-Bromo-6-ethoxynaphthalene (5.3 g) was dissolved in THF (40 ml) and magnesium (0.515 g) and methyl iodide (one drop) were added and the mixture was vigorously stirred to dissolve magnesium. The reaction mixture was ice-cooled and a solution of 4-formyl-1-tritylimidazole (7 g) in THF (80 ml) was added dropwise over 30 min. The mixture was stirred at room temperature for 1 h. To the reaction mixture were added saturated aqueous solution (40 ml) of ammonium chloride and water (40 ml) and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated. The residue was washedwith ethyl acetate to give (6-ethoxynaphthalen-2-yl)-(1-trityl-1H-imidazol-4-yl)methanol (6.3 g) as a colorless powder.
  • 26
  • [ 37593-02-5 ]
  • [ 7664-93-9 ]
  • [ 66217-19-4 ]
  • ammonium chloride [ No CAS ]
  • 1-(4-pentylphenyl)-1-(6-ethoxy-2-naphthyl)ethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium In tetrahydrofuran 1.a Example 1 (a) 0.2 mol of 2-bromo-6-ethoxynaphthalene are added dropwise in 200 ml of THF to 0.22 mol of magnesium turnings. The mixture is heated to reflux for a further 1 hour and cooled to room temperature, and 0.21 mol of 4-pentylacetophenone in 50 ml of THF are added at 15°-20°. The mixture is stirred for a further 15 minutes at room temperature, hydrolyzed using saturated NH4 Cl solution and worked up by extraction. After evaporating the extract, 150 ml of 20% H2 SO4 is added to the residue and the mixture is heated to reflux for 1 hour. The reaction mixture is again worked up by extraction. Recrystallization from methanol/ethanol gives 1-(4-pentylphenyl)-1-(6-ethoxy-2-naphthyl)ethene.
  • 27
  • [ 66217-19-4 ]
  • [ 130305-57-6 ]
  • 1-benzyl-4-hydroxy-4-(6-ethoxynaphth-2-yl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
V 1-benzyl-4-hydroxy-4-(6-ethoxynaphth-2-yl)piperidine Preparation V 1-benzyl-4-hydroxy-4-(6-ethoxynaphth-2-yl)piperidine Beginning with 5.0 gm (19.9 mMol) 2-bromo-6-ethoxy- naphthalene, 4.65 gm (65%) of the title compound were recovered as a white solid by the procedure described in Preparation I.
  • 29
  • [ 74-96-4 ]
  • [ 66217-19-4 ]
  • [ 1999-63-9 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: ethyl bromide With magnesium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 2-ethoxy-6-bromo-naphthalene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 60℃; for 3h; Inert atmosphere;
  • 30
  • [ 66217-19-4 ]
  • [ 1377785-27-7 ]
  • (-)-2-ethoxy-6-ethyl-1,2,3,4-tetrahydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 1.2: 3 h / 60 °C / Inert atmosphere 2.1: hydrogen; N,N,N',N'-tetramethylguanidine / toluene / 48 h / 100 °C / 38002.6 Torr / Inert atmosphere
  • 31
  • [ 66217-19-4 ]
  • [ 16419-60-6 ]
  • [ 1377784-77-4 ]
YieldReaction ConditionsOperation in experiment
96% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In toluene at 80℃; for 24h; Inert atmosphere;
  • 32
  • [ 66217-19-4 ]
  • [ 98-80-6 ]
  • C18H20O [ No CAS ]
  • C18H20O [ No CAS ]
  • (-)-2-ethoxy-6-phenyl-1,2,3,4-tetrahydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate / toluene / 24 h / 80 °C / Inert atmosphere 2: hydrogen; N,N,N',N'-tetramethylguanidine / toluene / 48 h / 100 °C / 38002.6 Torr / Inert atmosphere
  • 33
  • [ 66217-19-4 ]
  • [ 98-80-6 ]
  • [ 858458-42-1 ]
YieldReaction ConditionsOperation in experiment
99% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In toluene at 80℃; for 24h; Inert atmosphere;
  • 34
  • [ 66217-19-4 ]
  • [ 1387543-48-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; triphenylphosphine / tetrahydrofuran / 15 h / 20 °C 2: methanol; potassium carbonate / tetrahydrofuran / 2 h
  • 35
  • [ 66217-19-4 ]
  • [ 1387543-54-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; triphenylphosphine / tetrahydrofuran / 15 h / 20 °C 2: methanol; potassium carbonate / tetrahydrofuran / 2 h 3: N,N,N,N,-tetramethylethylenediamine; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride / acetonitrile / 4 h / 20 °C
  • 36
  • [ 66217-19-4 ]
  • [ 1066-54-2 ]
  • [ 1387543-40-9 ]
YieldReaction ConditionsOperation in experiment
93.5% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In tetrahydrofuran at 78℃; for 20h; Inert atmosphere; 2 Under argon protection,In a 100 ml flask, 5.02 g (0.02 mol) of 2-bromo-6-ethoxynaphthalene and 41.156 g of Pd (PPh3)(1 mmol) of CuI, 0.191 g (1 mmol) of CuI and 30.262 g (1 mmol) of PPh. After the addition of argon, the atmosphere of the reaction flask was purged three times with the exception of 20 ml of triethylamine and 3.92 ml of trimethylethynylsilane mol), 30 ml of tetrahydrofuran.After the addition was completed, the system was allowed to rise to 78 ° C for 20 h.The reaction solution was filtered to remove a large amount of insoluble salts and solids to the filtrate150ml of methylene chloride was added to the solution and washed three times with 150ml of 5% diluted hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude sample was mixed with petroleum ether and passed through a silica gel column.After the column liquid was swirled to a white solid precipitation stopped rotating when placed at room temperature precipitated a large number of white solid, filtered and dried to give a white solid6-ethoxy-2-naphthylethynyltrimethylsilane 5.02 g, yield 93.5%
64% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran at 20℃; for 15h;
  • 37
  • [ 4028-63-1 ]
  • [ 66217-19-4 ]
  • C21H22O [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: iodomesitylene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With dimethylaluminum chloride In diethyl ether; hexane; pentane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #3: 2-ethoxy-6-bromo-naphthalene In tetrahydrofuran at 110℃; for 24h; Inert atmosphere; chemoselective reaction;
  • 38
  • [ 66217-19-4 ]
  • C12H11IO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-ethoxy-6-bromo-naphthalene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere;
  • 39
  • [ 66217-19-4 ]
  • C19H18O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / pentane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 0 °C / Inert atmosphere 2.3: 24 h / 110 °C / Inert atmosphere
  • 40
  • [ 66217-19-4 ]
  • 6-(pyridin-4-yl)naphthalen-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 72 h / Reflux 2: boron tribromide / chloroform / 0 - 20 °C
  • 41
  • [ 66217-19-4 ]
  • 4-(6-hydroxynaphthalen-2-yl)-1-(4-((2-oxo-2H-chromen-7-yl)oxy)butyl)pyridin-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 72 h / Reflux 2.1: boron tribromide / chloroform / 0 - 20 °C 3.2: 24 h / 80 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran / 72 h / Reflux 2: boron tribromide / chloroform / 0 - 20 °C 3: N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere
  • 42
  • [ 66217-19-4 ]
  • [ 1692-15-5 ]
  • 4-(6-ethoxynaphthalen-2-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran; water for 72h; Reflux;
  • 43
  • [ 66217-19-4 ]
  • C26H21FO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triphenylphosphine; triethylamine / tetrahydrofuran / 20 h / 78 °C / Inert atmosphere 2: potassium carbonate / tetrahydrofuran; methanol / 4 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triphenylphosphine; triethylamine / tetrahydrofuran / 30 h / 78 °C / Inert atmosphere
  • 44
  • [ 66217-19-4 ]
  • [ 677-22-5 ]
  • C16H20O [ No CAS ]
  • 2-(tert-butyl)-6-ethoxynaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With nickel chloride hydrate at -10℃; for 0.5h; General Procedural for the cross-coupling of aryl halide and tertiary alkylmagnesium halides. General procedure: To a mixture of aryl halide (0.3 mmol), NiCl2(H2O)1.5 [1] (0.0075 mmol, 2.5 mol %), was charged dry THF (1 mL). The mixture was pumped and refilled with nitrogen for three times. The resulting mixture was stirred at -10 under nitrogen for 30 min. The reaction mixture was quenched through the addition of ice MeOH, then poured into a separatory funnel containing saturated aqueous NH4Cl (ca. 5 mL) and extracted with EtOAc (3 x 5 mL). The combined organic layers were washed with brine and dried over Na2SO4. The crude product was purified by column chromatography. Extent of isomerization can be easily determined via 1H NMR spectroscopy by comparison of the intergral of the singlet from the t-butyl group (1.3-1.4 ppm, 9H) to the integral of the doublet from the benzylic S3 protons of the i-butyl group (2.4-2.5 ppm, 2H). The doublet from the methyls of the i-butyl group could additionally be used (ca. 0.8 ppm, 6H).
  • 45
  • [ 66217-19-4 ]
  • [ 73183-34-3 ]
  • 2-(6-ethoxynaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,2-dichloro-ethane at 80℃; for 18h;
  • 46
  • [ 66217-19-4 ]
  • 4-(4-(6-ethoxynaphthalen-2-yl)-2-(2-methyl-4-(methylsulfonyl)-phenyl)-1H-imidazol-5-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dichloro-ethane / 18 h / 80 °C 2.1: palladium diacetate; (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / 1,2-dichloro-ethane / 0.08 h / 20 °C / Inert atmosphere 2.2: 18.08 h / 20 - 80 °C / Inert atmosphere
  • 47
  • [ 66217-19-4 ]
  • C28H25FO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / 80 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate / 0.5 h / 20 °C 2.2: 4 h 3.1: potassium carbonate; potassium iodide / acetonitrile / 12 h / 20 °C
  • 48
  • [ 66217-19-4 ]
  • C19H17ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / 80 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate / 0.5 h / 20 °C 2.2: 4 h
  • 49
  • [ 66217-19-4 ]
  • 2-(4-((3-(6-ethoxynaphthalen-2-yl)benzyl)oxy)-2-fluorophenoxy)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / 80 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate / 0.5 h / 20 °C 2.2: 4 h 3.1: potassium carbonate; potassium iodide / acetonitrile / 12 h / 20 °C 4.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C
  • 50
  • [ 66217-19-4 ]
  • [ 87199-16-4 ]
  • C19H16O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 24h; Inert atmosphere; General procedure: The solution of 3a (600mg, 2.79mmol), (3-formylphenyl)boronic acid (460mg, 3.07mmol), Pd(PPh3)4 (390mg, 0.33mmol) and sodium carbonate (870mg, 8.37mmol) in toluene/ethanol/H2O (35mL, 3/1/3) was refluxed under nitrogen atmosphere for 24h. Then the mixture was diluted with saturated ammonium chloride solution and ethyl acetate, and the insoluble material was filtered through Celite. The organic layer of the filtrate was washed with water (25mL) and brine (25mL), dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography using a mixture of petroleum ether /ethyl acetate (10:1, v/v) as eluent to afford the desired product 4a 450mg (yield: 67%) as a white solid.
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