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3-(2,6-dibutyl-4-methylphenoxy)-4,5-bis(4-cyanophenoxy)-6-fluorophthalonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78.3 mol%
With potassium fluoride; In acetone;
SYNTHESIS EXAMPLE 4 Synthesis of 3-(2,6-dibutyl-4-methylphenoxy)-4,5-bis(4-cyanophenoxy)-6-fluorophthalonitrile In a four-neck separable flask having an inner volume of 500 ml, 60 g (0.30 mol) of <strong>[1835-65-0]tetrafluorophthalonitrile</strong>, 41.8 g (0.72 mol) of potassium fluoride, and 160 ml of acetone. Further, to a dropping funnel attached thereto, 71.5 g (0.60 mol) of 4-cyanophenol and 110 ml of acetone were placed. The 4-cyalophenol/acetone mixed solution was added dropwise from the dropping funnel to the flask over a period of about two hours while kept stirred at -1° C. The stirring was subsequently continued for about two hours. Thereafter, the contents of the flask were stirred overnight, with the reaction temperature thereof slowly raised to room temperature. Then, to this flask, 79.8 g (0.30 mol) of 2,6-dibutyl-4-methylphenol, 20.9 g (0.36 mol) of potassium fluoride, and 15.0 mol of acetone were charged and the mixture was kept stirred at 40° C. for 10 hours. The reaction solution was cooled and filtered. The filtrate was distilled by a rotary evaporator to expel the acetone and was recrystallized from methanol. The produced crystals were separated by filtration and vacuum dried to afford 151.3 g of 3-(2,6-dibutyl-4-methylphenoxy)-4,5-bis(4-cyanophenoxy)-6-fluorophthalonitrile (yield: 78.3 mol percent).
3-(2,6-dimethylphenoxy)-4,5-bis(4-cyanophenoxy)-6-fluorophthalonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
77.5 mol%
With potassium fluoride; In acetone;
SYNTHESIS EXAMPLE 5 Synthesis of 3-(2,6-dimethylphenoxy)-4,5-bis(4-cyanophenoxy)-6-fluorophthalonitrile In a four-neck separable flask having an inner volume of 500 ml, 60 g (0.30 mol) of <strong>[1835-65-0]tetrafluorophthalonitrile</strong>, 41.8 g (0.72 mol) of potassium fluoride, and 160 ml of acetone. Further, in a dropping funnel attached thereto, 71.5 g (0.60 mol) of 4-cyanophenol and 110 ml of acetone were placed. The 4-cyalophenol/acetone mixed solution was added dropwise from the dropping funnel to the flask over a period of about two hours while kept stirred at -1° C. The stirring was subsequently continued for about two hours. Thereafter, the contents of the flask were stirred overnight, with the reaction temperature thereof slowly raised to room temperature. Then, to this flask, 36.7 g (0.30 mol) of 2,6-dimethylphenol, 20.9 g (0.36 mol) of potassium fluoride, and 15.0 ml of acetone were charged and the mixture was kept stirred at 40° C. for 10 hours. The reaction solution was cooled and filtered. The filtrate was distilled by a rotary evaporator to expel the acetone and was recrystallized from methanol. The produced crystals were separated by filtration and vacuum dried to afford 116.3 g of 3-(2,6-dimethylphenoxy)-4,5-bis(4-cyanophenoxy)-6-fluorophthalonitrile (yield: 77.5 mol percent).
With potassium carbonate; In ethanol; water; at 80℃; for 16h;
A mixture of 1-chloro-2-methyl-propan-2-ol (10 mL ), 4-hydroxybenzonitrile (2 g, 16.8 mmol), K2CO3 (9.3 g, 67.3 mmol) in water (6 mL) and ethanol (60 mL) was heated at 80 °C for 16 hours. The reaction mixture was cooled and the solvent was concentrated in vacuo. The residue was diluted with ether (200 mL) and filtered and the filtrate was washed sequentially with water (50 mL) and brine solution (50 mL). The organics were separated and dried over MgSO4 and solvent was removed in vacuo to give a residue which was purified by silica gel column chromatography using (0-100percent) EtOAc/DCM as eluent to give 4-(2-hydroxy- 2-methyl-propoxy)benzonitrile (3.0 g, 94 percent) as a yellow solid. ESI-MS m/z calc. 191.1, found 192.3 (M+1)+; Retention time: 1.05 minutes (3 min run).
methyl 4-(1-(4-cyanophenoxy)ethyl)benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
45%
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 12h;
Methyl 4-(l-(4-cyanophenoxy)ethyl)benzoate. Methyl 4-(l -hydroxy ethyl)benzoate (540 mg, 3 mmol), 3-hydroxybenzonitrile (360 mg, 3 mmol), triphenylphosphine (1.04 mg, 4 mmol), azodicarboxylic acid diisopropyl ester (800 mg, 4 mmol) in tetrahydrofuran (130 mL) were stirred at 20C for 12 hours. Water was added and the mixture was extracted with ethyl acetate (150 mL x 3), the combined organic phase was dried by sodium sulfate, then filtered. The filtrate was evaporated in vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 3: 1) to give methyl 4-(l-(4- cyanophenoxy)ethyl)benzoate (370 mg, 45%) as colorless oil. LRMS (M + H+) m/z: calcd 281.11; found 281.).
With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; under 2400.24 Torr; for 0.5h;Microwave irradiation;
Tert-butyl 4-(4-cyanophenoxy)benzoate. To a solution of tert-butyl 4- fluorobenzoate (392 mg, 2 mmol) in dimethyl formamide (20 mL) was added 4- hydroxybenzonitrile (240 mg, 2 mmol) and potassium carbonate (552 mg, 4 mmol), the mixture was heated to 130C for 0.5 hour by microwave (pressure: 3.2 bar, equipment power : 150W). The solvent was evaporated in vacuo and purified by column chromatography (silica gel, dichloromethane/methanol = 20: 1) to give tert-butyl 4-(4-cyanophenoxy)benzoate (80 mg, 14%). LRMS (M + H+) m/z: calcd 295.12; found 295.
14%
With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; under 2400.24 Torr; for 0.5h;Microwave irradiation;
To a solution of <strong>[58656-98-7]ter<strong>[58656-98-7]t-butyl 4-fluorobenzoate</strong></strong> (392 mg, 2 mmol) in dimethyl formamide (20 mL) was added 4-hydroxybenzonitrile (240 mg, 2 mmol) and potassium carbonate (552 mg, 4 mmol), the mixture was heated to 130 C. for 0.5 hour by microwave (pressure: 3.2 bar, equipment power: 150 W). The solvent was evaporated in vacuo and purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give tert-butyl 4-(4-cyanophenoxy)benzoate (80 mg, 14%). LRMS (M+H+) m/z: calcd 295.12. found 295.
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