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CAS No. : | 155820-88-5 | MDL No. : | MFCD10697865 |
Formula : | C8H6BrF3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 239.03 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 | UN#: | N/A |
Hazard Statements: | H227-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(l) iodide In N,N-dimethyl-formamide at 70℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide at 70℃; for 4h; | |
64 %Spectr. | With potassium fluoride; 18-crown-6 ether In water; N,N-dimethyl-formamide at 80 - 140℃; sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In 1-methyl-pyrrolidin-2-one at 20 - 80℃; | 40A 1-Bromo-4-(2,2,2-trifluoroethyl)benzene Example 40A 1-Bromo-4-(2,2,2-trifluoroethyl)benzene A solution of 25.0 g (100 mmol) of 4-bromobenzyl bromide in 1-methyl-2-pyrrolidone (121 ml) was admixed at RT with 4.95 g (26.0 mmol) of copper(I) iodide and 37.5 g (195 mmol) of methyl 2,2-difluoro-2-(fluorosulphonyl)acetate. The mixture was heated to 80° C. and then stirred overnight. The reaction solution was added to water and extracted with diethyl ether, and the organic phase was dried over sodium sulphate. After filtering and concentrating the organic phase under reduced pressure, the residue was purified by means of column chromatography (silica gel, cyclohexane/ethyl acetate 20:1). Yield: 16.1 g (67% of theory) GC-MS (Method 1F): Rt=2.66 min; MS (ESIpos): m/z=240 [M+H]+. |
67% | In 1-methyl-pyrrolidin-2-one at 20 - 80℃; | 51A 1-bromo-4-(2,2,2-trifluoroethyl)benzene Example 51A1-Bromo-4-(2,2,2-trifluoroethyl)benzene A solution of 25.0 g (100 mmol) of 4-bromobenzyl bromide in 1-methyl-2-pyrrolidone (121 ml) was admixed at RT with 4.95 g (26.0 mmol) of copper(I) iodide and 37.5 g (195 mmol) of methyl 2,2-difluoro-2-(fluorosulphonyl)acetate. The mixture was heated to 80° C. and then stirred overnight. The reaction solution was added to water and extracted with diethyl ether, and the organic phase was dried over sodium sulphate. After filtering and concentrating the organic phase in vacuo, the residue was purified by means of column chromatography (silica gel, cyclohexane/ethyl acetate 20:1). Yield: 16.1 g (67% of theory)GC-MS (Method 1F): Rt=2.66 min; MS (ESIpos): m/z=240 [M+H]+. |
With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / pyridine / 0.17 h / 0 - 10 °C 2: 72 percent / CuI / dimethylformamide / 8 h / 70 °C | ||
Multi-step reaction with 2 steps 1.1: sodium hydride; 1H-imidazole / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 1.3: 20 °C / Inert atmosphere 2.1: copper / acetonitrile / 9 h / 60 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C 1.2: 1 h / 20 °C 2.1: methyl iodide / N,N-dimethyl-formamide / 1 h / 20 °C 2.2: 15 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In N,N-dimethyl-formamide at 100℃; for 18h; | I-17 Example 1-17 4-f2,2,2-Trifluoroethyl)benzonitrile; Intermediate 17 To the DMF (25 mL) solution of l-bromo-4-(2,2,2-trifiuoroethyl)benzene (2.15 g, 9.00 mmol) were zinc cyanide (2.11 g, 18.0 mmol) then Pd(PPh3)4 (0.828 g, 0.720 mmol) added. The mixture was heated at 1000C for 18 hours then cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a short bed of celite. The filtrate was concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using hexane : ethyl acetate = 90:10 as eluent to give the title compound as a white solid, 800 mg (48%). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.67 (d, 2 H) 7.43 (d, 2 H) 3.44 (q, 2 H). 19F NMR (400 MHz, CDCl3) δ (ppm) -65.85, -65.88 and -65.91. MS (ESI) m/z 186 [M+H]. |
48% | With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 18h; | |
48% | In DMF (N,N-dimethylformamide) at 100℃; for 18h; | I-31 To the DMF (25 niL) solution of l-bromo-4-(2,2,2-trifluoroethyl)benzene (2.15 g, 9.00 mmol) were zinc cyanide (2.11 g, 18.0 mmol) and Pd(PPh3)4 (0.828 g, 0.720 mmol) added. The mixture was heated at 1000C for 18 hours then cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a short bed of celite. The filtrate was concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using hexane : ethyl acetate = 90: 10 as eluent to give the title compound as a white solid, 800 mg (48%).1H NMR (400 MHz, CDCl3) δ (ppm) 7.67 (d, 2 H) 7.43 (d, 2 H) 3.44 (q, 2 H). 19F NMR (400 MHz, CDCl3) δ (ppm) -65.85, -65.88 and -65.91. MS (ESI) m/z 186 [M+H]. |
48% | In DMF (N,N-dimethylformamide) at 100℃; for 18h; | I-16 To the DMF (25 mL) solution of l-bromo-4-(2,2,2-trifluoroethyl)benzene (2.15 g, 9.00 mmol) were zinc cyanide (2.11 g, 18.0 mmol) then Pd(PPh3)4 (0.828 g, 0.720 mmol) added. The mixture was heated at 1000C for 18 hours then cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a short bed of celite. The filtrate was concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using hexane : ethyl acetate = 90:10 as eluent to give the title compound as a white solid, 800 mg (48%). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.67 (d, 2 H) 7.43 (d, 2 H) 3.44 (q, 2 H). 19F NMR (400 MHz, CDCl3) δ (ppm) -65.85, -65.88 and -65.91. MS (ESI) m/z 186 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: [5-(methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride; 1-bromo-4-(2,2,2-trifluoroethyl)benzene With potassium fluoride; potassium carbonate In ethanol; water; toluene at 20℃; for 8h; Inert atmosphere; Reflux; Stage #2: for 8h; Reflux; | 52A methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate Example 52AMethyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate A solution of 8.00 g (33.5 mmol) of the compound from Example 51A in toluene (304 ml) was admixed under argon at RT with 10.9 g (50.2 mmol) of the compound from Example 29A in ethanol (100 ml) and 5.10 g (36.8 mmol) of potassium carbonate. After stirring for 10 min, 3.87 g (3.35 mmol) of tetrakis(triphenylphosphine)palladium and then 5.83 g (100 mmol) of potassium fluoride in water (64 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 100:1→80:1). Yield: 9.20 g (69% of theory, purity 75%)LC-MS (Method 6B): Rt=1.06 min; MS (ESIpos): m/z=296 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With potassium fluoride; potassium carbonate In ethanol; water; toluene at 20℃; for 8h; Reflux; | 41A Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate Example 41A Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate A solution of 8.00 g (33.5 mmol) of the compound from Example 40A in toluene (304 ml) was admixed under argon at RT with 10.9 g (50.2 mmol) of the compound from Example 33A in ethanol (100 ml) and 5.10 g (36.8 mmol) of potassium carbonate. After stirring for 10 min, 3.87 g (3.35 mmol) of tetrakis(triphenylphosphine)palladium and then 5.83 g (100 mmol) of potassium fluoride in water (64 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 100:1→80:1). Yield: 9.20 g (69% of theory, purity 75%) LC-MS (Method 5B): Rt=1.06 min; MS (ESIpos): m/z=296 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate; potassium fluoride / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 20 °C / Inert atmosphere; Reflux 1.2: 8 h / Reflux 2.1: hydrogen / palladium 10% on activated carbon; platinum(IV) oxide / concentrated acetic acid / 6 h / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With triethylamine In 1,4-dioxane; water at 80℃; for 7.5h; Inert atmosphere; | 5.27 Reference Example 5-27 4,4,5,5-Tetramethyl-2-[4-(2,2,2-trifluoroethyl)phenyl]-1,3,2-dioxaborolane A solution of 1-bromo-4-(2,2,2-trifluoroethyl)benzene (510 mg), bis(pinacolato)diborane (1.08 g), a 1,1'-bis(diphenylphosphino)ferrocenepalladium chloride-dichloromethane complex (70 mg) and triethylamine (1.2 mL) in 1,4-dioxane (10 mL) was stirred at 80° C. for 7.5 hours in a nitrogen atmosphere. The reaction solution was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→10:1) to give the title compound as a colorless solid (68 mg, 12%). 1H NMR (300 MHz, CDCl3) δ ppm 1.34 (s, 12H), 3.37 (q, J=10.9 Hz, 2H), 7.29 (d, J=7.2 Hz, 2H), 7.80 (d, J=8.1 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / 16 h / -15 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / DMF (N,N-dimethylformamide) / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / -20 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux | ||
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / DMF (N,N-dimethylformamide) / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux | ||
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / DMF (N,N-dimethylformamide) / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / 16 h / -15 - 20 °C / Inert atmosphere 5.1: methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60 %Spectr. | With copper In acetonitrile at 60℃; for 9h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With ammonium chloride; lithium hydroxide at 100℃; for 24h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
203 mg | Stage #1: 4-bromobenzyl diphenylphosphinite With methyl iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2,2-difluoro-2-(fluorosulfonyl)acetate With copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 15h; | 3 4.3. General procedure for the preparation of compound 3 General procedure: To a stirred solution of benzyl or allyl alcohol (1, 1.5 mmol) in THF (10 mL) was added n-BuLi (1.6 M in hexane, 0.95 mL) at 0 °C. The mixture was warmed to room temperature. After stirring for 1 h, a solution of Ph2PCl (1.5 mmol) in THF (5 mL) was added at 0 °C, and the resulted mixture was continuously stirred at room temperature for 1 h and quenched with water after completion ofthe reaction (detected by TLC). The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate. Compound 2 was obtained after filtration and evaporation. To a solution of 2 in DMF (10 mL) was added CH3I (4.5 mmol) at room temperature. After stirring for 1 h, methyl fluorosulfonyldifluoroacetate (4.5 mmol) and CuI (0.30 mmol) were added. The mixture was heated and stirred at 80 °C for 15 h. Then the reaction was quenched with water and the resulting mixture was extracted with diethyl ether. The extract was dried over sodium sulfate. After removal of solvent, the crude product was purified by chromatography on silica gel to give 3 (eluent: n-hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 6.1: aluminum (III) chloride; ethanethiol / dichloromethane / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 6.1: aluminum (III) chloride; ethanethiol / dichloromethane / 4 h / 0 - 20 °C 7.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation |
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