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With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;
To a mixture of <strong>[58743-79-6]4-bromo-4'-ethylbiphenyl</strong> (748 mmol) and 500 ml of THF was added dropwise 500 ml of a solution of n-butyl lithium (corresponding to 785 mmol) in hexane at -78 C. in 1.5 hours, and stirred at the same temperature for 2.0 hours. To this solution was added dropwise 150 ml of a solution of trimethyl borate (1,496 mmol) in THF, the solution was gradually warmed up to room temperature, and then the solution was stirred overnight. After 750 ml of 7.3% hydrochloric acid was added and stirred for 30 min, the reaction solution was extracted twice with diethyl ether, washed thrice with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was recrystallized from about 1,600 ml of toluene and 500 ml of acetone to give a white solid of 4'-ethylbiphenyl-4-boric acid (572 mmol).
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;
To a mixture of <strong>[58743-79-6]4-bromo-4'-ethylbiphenyl</strong> (748 mmol) and 500 ml of THF was added dropwise 500 ml of a solution of n-butyl lithium (corresponding to 785 mmol) in hexane at -78 C. in 1.5 hours, and stirred at the same temperature for 2.0 hours. To this solution was added dropwise 150 ml of a solution of trimethyl borate (1,496 mmol) in THF, the solution was gradually warmed up to room temperature, and then the solution was stirred overnight. After 750 ml of 7.3% hydrochloric acid was added and stirred 30 min, the reaction solution was extracted twice with diethyl ether, washed thrice with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was recrystallized from about 1,600 ml of toluene and 500 ml of acetone to obtain white solid of 4'-ethylbiphenyl-4-boric acid (572 mmol).
With potassium carbonate;5%-palladium/activated carbon; In ethanol; water; toluene; for 6h;Heating / reflux;
A mixture of 5.6 g (21.4 mmol) of <strong>[58743-79-6]4-bromo-4'-ethylbiphenyl</strong>, 3.6 g (25.7 mmol) of 3-fluorophenyl dihydroxyborane, 4.4 g (32.2 mmol) of potassium carbonate, 0.3 g of 5%-Pd/C and 60 mL of a mixed solvent of toluene, ethanol and water (ratio: 1/1/1) was refluxed for 6 hours to obtain a reaction solution. After removing the catalyst by filtration, 50 mL of toluene was added to the reaction solution, which was then washed with water. The reaction solution having been washed with water was dried over anhydrous magnesium sulfate, and the solvent was distilled off from the reaction solution under reduced pressure to obtain 8.6 g of a residue. The residue was purified by silica gel column chromatography (eluent: heptane/toluene = 4/1) to obtain 5.1 g of crude crystals of the compound (E-8). The crude crystals were dissolved in a mixed solvent of ethanol and ethyl acetate (ratio: 10/1) and recrystallized therefrom to obtain 4.5 g of purified crystals of the compound (E-8).
4‐{4'‐ethyl‐[1,1'‐biphenyl]‐4‐yl}‐2‐methylbut‐3‐yn‐2‐ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine;Inert atmosphere; Reflux;
261.16 mg (1 mmol) of <strong>[58743-79-6]4'-bromo-4-ethylbiphenyl</strong> and 100 muL (1 mmol)2-methyl-3-butyn-2-ol and 7 mgtwoTriphenylphosphine palladium dichloride,15 mg triphenylphosphine,8 mg of CuI were added as a catalyst to a 50 mL two-necked round bottom flask,With 15 mL of dry triethylamine as the acid binding agent and solvent. Nitrogen under the conditions of mixing,Heated to reflux to complete the reaction. The triethylamine was removed under reduced pressure,The crude product was passed through a silica gel column (eluent: dichloromethane)The solvent was removed under reduced pressure to give a white solid in 92% yield.
92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine;Inert atmosphere; Reflux;
1 mmol of <strong>[58743-79-6]4'-bromo-4-ethylbiphenyl</strong> and 100 muL (1 mmol) of 2-methyl-3-butyn-2-ol and 7 mg of dibenzene Base phosphine dichloride,15 mg triphenylphosphine,8 mg of CuI were added as a catalyst to a 50 mL two-necked round bottom flask,With 15 mL of dry triethylamine as the acid binding agent and solvent. Nitrogen under the conditions of mixing,Heated to reflux to complete the reaction. The triethylamine was removed under reduced pressure,The crude product was passed through a silica gel column (eluent: dichloromethane)The solvent was removed under reduced pressure to give a white solid in 92% yield.
92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine;Inert atmosphere; Reflux;
302 mg (1 mmol) <strong>[58743-79-6]4'-bromo-4-ethylbiphenyl</strong> and 100 muL (1 mmol) 2-methyl-3-butyn-2-ol and 7 mg of triphenylphosphine palladium dichloride, 15 mg of triphenylphosphine, 8 mgCuI was added as a catalyst 50 mL double mouth round bottom flask, Use 15 mL of dry triethylamine as the acid binding agent and solvent. Nitrogen under the conditions of mixing, Heated to reflux to complete the reaction. The triethylamine was removed under reduced pressure, The crude product was passed through a silica gel column (eluent: dichloromethane) The solvent was removed under reduced pressure to give 281.7 mg of a white solid, Yield 92%. Melting point: 48.4-49.7 C.
92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine;Inert atmosphere; Reflux;
302 mg (1 mmol) of <strong>[58743-79-6]4'-bromo-4-ethylbiphenyl</strong>And 100 muL (1 mmol) of 2-methyl-3-butyn-2-olAnd 7 mg of ditriphenylphosphine palladium dichloride,15 mg of triphenylphosphine,8 mg of CuI was added as a catalyst to a 50 mL two-neck round bottom flask.15 mL of dry triethylamine was used as the acid binding agent and solvent.Stir under nitrogen atmosphere and heat to reflux to complete the reaction.The triethylamine was removed under reduced pressure, and the crude product was applied to silica gel column (eluent: dichloromethane).The solvent was removed under reduced pressure to give 281.7 mg of white solid, 4 -{4'-ethyl-[1,1'-biphenyl]-4-yl}-2-methylbut-3-yn-2-Ol, yield 92%.
4-(1,1-difluoroethyl)-4'-ethyl-1,1'-biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
58%
With dmap; bis(tricyclohexylphosphine)nickel(II) dichloride; 4,4'-diamino-2,2'-bipyridyl; magnesium chloride; zinc; In dimethyl sulfoxide; at 110℃; for 10h;Schlenk technique;
To a 10 ml Schlenk reaction tube, add <strong>[58743-79-6]4-bromo-4'-ethylbiphenyl</strong> (0.2 mmol),Bis (tricyclohexylphosphine) nickel dichloride (10 mol%), 4,4?-diamino-2,2?-bipyridine (10 mol%),4-dimethylaminopyridine (20 mol%), magnesium chloride (3 equivalents), zinc powder (2 equivalents),Evacuate and change the nitrogen, and then dissolve the DMSO solution of reactant 1(Before the reaction is ready, pass reactant 1 slowly into DMSO until the total volume does not increase, and the concentration is 0.7 mol / L after 19F NMR detection) Add 1mL,The reaction was carried out at 110 C for 10h. After the reaction was completed, the reaction was detected by TLC, and the target product was obtained by column chromatography (58%).