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2,5-difluoro-4-nitro-4'-(trans-4-pentylcyclohexyl)biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84.4%
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 12h;Heating / reflux;
(7-a) Synthesis of compound 2,5-difluoro-4-nitro-4'-(trans-4-pentylcyclohexyl)biphenyl represented by formula: First, 50 ml of ethanol containing 7.52 g of <strong>[143651-26-7]4-(trans-4-pentylcyclohexyl)phenylboronic acid</strong> dissolved therein, 50 ml of benzene containing 5.0 g of 4-bromo-2,5-difluoro-1-nitrobenzene dissolved therein, 21.0 ml of a sodium carbonate aqueous solution with a concentration of 2.0 mol/l, and 0.61 g of tetrakis(triphenylphosphine)palladium(0) were put in an argon-replaced 200 ml flask, and stirred under reflux for 12 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:toluene/hexane=1/4) and recrystallized from hexane, to obtain 6.87 g (Y: 84.4%) of 2,5-difluoro-4-nitro-4'-(trans-4-pentylcyclohexyl)biphenyl.. The purity of the resultant compound was 100.0% as measured by GC. The phase transfer temperature of the compound was as follows.
methyl 1-(5-bromo-4-fluoro-2-nitrophenoxy)cyclopropanecarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a mixture of <strong>[33689-29-1]methyl 1-hydroxycyclopropanecarboxylate</strong> (Aldrich) (1.0 g, 8.8 mmol) and 15-crown-5 (cat. amount) in THF (30 ml) was added NaH (400 mg, 10 mmol) at room temperature. The resulting mixture was stirred at room temperature for 30 min and then added 1-bromo-2,5-difluoro-4-nitrobenzene (Aldrich) (2 g, 8.4 mmol). The mixture was stirred at room temperature for additional 16 hrs. When TLC indicated the reaction was completed, the reaction mixture was quenched with saturated NH4Cl aqueous solution. After removal of the organic solvent, the mixture was extracted with ethyl acetate (*3). The combined organic phases were washed with brine (*3), dried over anhydrous Magnesium sulfate and filtered. The filtration was concentrated under reduced pressure to give the crude product, which was purified by flash column chromatography on silica gel using a gradient 0-10% ethyl acetate in hexanes to afford the title compound as yellow solid. LC-MS: Rt=1.43 mins; MS m/z [M+H]+ 333.9; Method 5-95AB 1.5minLC_v003 1H NMR (400 MHz, CDCl3) delta 8.15 (1H, d), 6.98 (1H, d), 3.57 (3H, s), 1.38 (2H, m), 1.18 (2H, m).
Step 1 : methyl 1-(5-bromo-4-fluoro-2-nitrophenoxy)cvclopropanecarboxylate: To a mixture of <strong>[33689-29-1]methyl 1-hydroxycyclopropanecarboxylate</strong> (Aldrich) (1.0 g, 8.8 mmol) and 15- crown-5 (cat. amount) in THF (30 ml) was added NaH (400 mg, 10 mmol) at room temperature. The resulting mixture was stirred at room temperature for 30 min and then added 1-bromo-2,5- difluoro-4-nitrobenzene (Aldrich) (2 g, 8.4 mmol). The mixture was stirred at room temperature for additional 16 hrs. When TLC indicated the reaction was completed, the reaction mixture was quenched with saturated NH4CI aqueous solution. After removal of the organic solvent, the mixture was extracted with ethyl acetate (x3). The combined organic phases were washed with brine (x3), dried over anhydrous Magnesium sulfate and filtered. The filtration was concentrated under reduced pressure to give the crude product, which was purified by flash column chromatography on silica gel using a gradient 0-10% ethyl acetate in hexanes to afford the title compound as yellow solid. LC-MS: Rt=1.43 mins; MS m/z [M+H]+ 333.9; Method 5-95AB 1.5minLC_v003 1H NMR (400 MHz, CDCI3) delta 8.15 (1 H, d), 6.98 (1 H, d), 3.57 (3H, s), 1.38 (2H, m), 1.18 (2H, m).
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