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4-bromo-3-fluoro-4'-(trans-4-pentylcyclohexyl)biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86.8%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 16h;Heating / reflux;
(6-a) Synthesis of compound 4-bromo-3-fluoro-4'-(trans-4-pentylcyclohexyl)biphenyl represented by formula: First, 100 ml of ethanol containing 11.89 g of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> dissolved therein, 100 ml of benzene containing 10.0 g of 1-bromo-2-fluoro-4-iodobenzene dissolved therein, 33.2 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.96 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 500 ml flask, and stirred under reflux for 16 hours.. After the reaction, water and ether were added to the reaction solution for extraction.. The resultant ether layer was washed with a saturated brine and dried with sodium sulfate.. The solvent was then distilled off.. The residue was purified by silica gel column chromatography (eluent:hexane) and recrystallized from acetone, to obtain 11.6 g (Y: 86.8%) of 4-bromo-3-fluoro-4'-(trans-4-pentylcyclohexyl)biphenyl.. The purity of the resultant compound was 100.0% as measured by GC.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 60℃; for 8h;
14.3 g (61.0 mmol) of <strong>[133997-05-4]4-octylphenylboronic acid</strong>, 16.7 g (55.5 mmol) of 1-bromo-2-fluoro-4-iodobenzene, 200 ml of dimethoxyethane, 19.4 g (0.183 mol) of sodium carbonate, 200 ml of pure water, 1.0 g (0.86 mmol) of tetrakis(phenylphosphine)palladium (0) were placed in a flask. The resulting mixture was stirred at 60 C. for 8 hours. Pure water was added to the reaction mixture and extracted with dichloromethane. The solvent in an organic phase was removed with hexane, whereby a crude product of compound (o) was obtained.This crude product was purified by column chromatography, whereby 18.2 g (yield: 90%) of compound (o) was obtained.
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In 1,4-dioxane; water; at 80℃; for 6h;Inert atmosphere;
A mixture of 1 -bromo-2-fluoro-4-iodobenzene (460 mg, 1.5 mmol, 1.0 equiv), <strong>[216019-28-2]3-isopropylphenyl-boronic acid</strong> (250 mg, 1.5 mmol, 1.0 equiv), Pd(PPh3)2C12 (35 mg, 0.05 mmol, 0.03 equiv) and NaHCO3 (640 mg, in 4 mE water) were added to a flask and dioxane (4 mE) was added. The mixture was purged with argon for 5 mm, and then stirred at 80 C. under an argon atmosphere for 6 h. The reaction was diluted with ethyl acetate (200 mE), washed with 60 mE water, then 40 mE brine, dried and concentrated. Purification via silica gel colunm chromatography with (gradient of 0-2. 5% ethyl acetate/hexanes) gave desired the biphenyl bromide as yellow oil 340 mg. The biphenyl bromide was converted to 289 by Method 1. [M-H]357.1 mlz. Activity: A
tert-butyl 3-(4-bromo-3-fluorophenyl)-3-hydroxycyclobutane-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
54%
To a 100 mL 3 -necked round-bottom flask was added a solution of l-bromo-2-fluoro-4- iodobenzene 40a (1 g, 3.32 mmol, 1.00 equiv.) in tetrahydrofuran (10.4 mL). A 2M solution of i-PrMgCl in THF (1.7 mL, 1.00 equiv) was added dropwise with stirring at 0°C during a 30 min period. The reaction mixture was stirred for another 3h at 0°C, then cooled to -70°C, and added with tert-Butyl 3-oxocyclobutane-l-carboxylate 40b (570 mg, 3.35 mmol, 1.00 equiv.) dropwise in 10 min. The resulting mixture was stirred at -78°C for lh, and continued at room temperature overnight. Water was added, the mixture was extracted with ethyl acetate (250 mL x 2), and the combined organic extracts were washed with a saturated H4CI aqueous solution (250 mL x 3), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 : 15) to afford tert-butyl 3 -(4-bromo-3-fluorophenyl)-3 -hydroxy cyclobutane-l-carboxylate 40c (620 mg, 54percent) as a light yellow oil.
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