Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 434-42-4 | MDL No. : | MFCD12789673 |
Formula : | C8H6BrF3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IRICHAOGAOFEQI-UHFFFAOYSA-N |
M.W : | 239.03 | Pubchem ID : | 14438709 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.28 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.18 cm/s |
Log Po/w (iLOGP) : | 2.13 |
Log Po/w (XLOGP3) : | 3.63 |
Log Po/w (WLOGP) : | 4.62 |
Log Po/w (MLOGP) : | 3.85 |
Log Po/w (SILICOS-IT) : | 3.53 |
Consensus Log Po/w : | 3.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.85 |
Solubility : | 0.034 mg/ml ; 0.000142 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.32 |
Solubility : | 0.115 mg/ml ; 0.000481 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.19 |
Solubility : | 0.0154 mg/ml ; 0.0000644 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triphenyl phosphite; N-Bromosuccinimide In dichloromethane at 40℃; for 12h; | |
45% | With triphenyl phosphite; N-Bromosuccinimide In 1,2-dichloro-ethane at -10 - 20℃; for 4h; | |
With phosphorus pentabromide at 165℃; |
With phosphorus pentabromide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide In benzene at 80℃; Irradiation; | ||
With N-Bromosuccinimide In benzene at 80℃; Irradiation; relative rate const. to toluene , m-CF3C6H4CH3 and XC6H5CH2CF3 (X= p-Cl, m-Cl m-CF3);isotopic effect; correlation between log k and Brown's const.; the method of competing reaction;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium bromide In diethylene glycol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate In ethanol at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With [2,2]bipyridinyl; copper(l) chloride In 1,2-dichloro-benzene at 180℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: 1-styrenyloxytrimethylsilane; 1,1,1-trifluoro-2-bromo-2-phenylethane With [2,2]bipyridinyl; 4 A molecular sieve; copper(l) chloride In 1,2-dichloro-benzene at 180℃; for 33h; Stage #2: With hydrogenchloride In diethyl ether; acetic acid at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [2,2]bipyridinyl; copper(l) chloride In 1,2-dichloro-benzene at 180℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: 2-Trimethylsiloxy-hepten-(1); 1,1,1-trifluoro-2-bromo-2-phenylethane With [2,2]bipyridinyl; 4 A molecular sieve; copper(l) chloride In 1,2-dichloro-benzene at 180℃; Stage #2: With hydrogenchloride In diethyl ether; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: carbon dioxide; 1,1,1-trifluoro-2-bromo-2-phenylethane With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at -40℃; Electrochemical reaction; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | ||
60% | With triphenyl phosphite; N-Bromosuccinimide In dichloromethane for 18h; Reflux; | Step 2. l-(l-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (All). General procedure: Step 2. l-(l-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (All). To a stirred solution of l-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (4.0 g, 16.3 mmol) in dichloromethane (CH2CI2; 50 mL), were added N-bromosuccinimide (NBS; 2.9 g, 16.3 mmol) and triphenyl phosphite (5.06 g, 16.3 mmol), and the resultant reaction mixture was heated at reflux for 18 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to 25 °C and was concentrated under reduced pressure. Purification by flash column chromatography (Si02, 100-200 mesh; eluting with 100% pentane) afforded the title compound as a liquid (2.0 g, 40%): ]H NMR (400 MHz, CDC13) δ 7.41 (s, 3H), 5.00 (m, IH); EIMS m/z 306 ([M]+). |
60% | With triphenyl phosphite; N-Bromosuccinimide In dichloromethane for 18h; Reflux; | (1-Bromo-2,2,2-trifluoroethyl)benzene (DI4) General procedure: To a stirred solution of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (4.0 g, 16.3 mmol) in CH2Cl2 (50 mL), were added N-bromosuccinimide (NBS; 2.9 g, 16.3 mmol) and triphenyl phosphite (5.06 g, 16.3 mmol), and the resultant reaction mixture was heated at reflux for 18 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to 25° C. and was concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 100% pentane) afforded the title compound as a liquid (2.0 g, 40%): 1H NMR (400 MHz, CDCl3) δ 7.41 (s, 3H), 5.00 (m, 1H); EIMS m/z 306 ([M]+). |
60% | With triphenyl phosphite; N-Bromosuccinimide In dichloromethane for 18h; Reflux; | 1-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (AI1) General procedure: To a stirred solution of l-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (4.0 g, 16.3 mmol) in dichloromethane (CH2CI2; 50 mL), were added N-bromosuccinimide (NBS; 2.9 g, 16.3 mmol) and triphenyl phosphite (5.06 g, 16.3 mmol), and the resultant reaction mixture was heated at reflux for 18 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to 25 °C and was concentrated under reduced pressure. Purification by flash column chromatography (Si02, 100-200 mesh; eluting with 100% pentane) afforded the title compound as a liquid (2.0 g, 40%): ]H NMR (400 MHz, CDC13) δ 7.41 (s, 3H), 5.00 (m, IH); EIMS m/z 306 ([M]+). |
60% | With N-Bromosuccinimide; triphenylphosphine In dichloromethane for 18h; Reflux; | Step 2. 1-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (AI1) General procedure: Step 2. 1-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (AI1) (0244) To a stirred solution of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (4.0 g, 16.3 mmol) in CH2Cl2 (50 mL), were added N-bromosuccinimide (NBS; 2.9 g, 16.3 mmol) and triphenyl phosphite (5.06 g, 16.3 mmol), and the resultant reaction mixture was heated at reflux for 18 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to 25° C. and was concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 100% pentane) afforded the title compound as a liquid (2.0 g, 40%): 1H NMR (400 MHz, CDCl3) δ 7.41 (s, 3H), 5.00 (m, 1H); EIMS m/z 306 ([M]+). |
60% | With N-Bromosuccinimide In dichloromethane for 18h; Reflux; | 1 Step 2. 1 -(1 -Bromo-2,2,2-trifluoroethyl)-3,5-dichlo- robenzene (C2) General procedure: Step 2. 1-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (C2) To a stirred solution of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (C1) (4.00 g, 16.3 mmol) in dichloromethane (50 mL), were added N-bromosuccinimide (2.90 g, 16.3 mmol) and triphenyl phosphite (5.06 g, 16.3 mmol), and the resultant reaction mixture was heated at reflux for 18 hours. After the reaction was deemed complete by thin layer chromatography, the reaction mixture was cooled to 25° C. and was concentrated under reduced pressure. Purification by flash column chromatography using 100% pentane as eluent afforded the title compound as a liquid (2.00 g, 40%) |
89 (1-Bromo-2,2,2-trifluoroethyl)benzene (DI4) (1-Bromo-2,2,2-trifluoroethyl)benzene (DI4) 2,2,2-Trifluoro-1-phenylethanol (DI3) was isolated (10 g, 80%): 1H NMR (300 MHz, CDCl3) δ 7.48 (m, 2H), 7.40 (m, 3H), 5.02 (m, 1H), 2.65 (d, J=7.1 Hz, 1H). The title compound (DI4) was isolated as a liquid (8.0 g, 60%): 1H NMR (400 MHz, CDCl3) δ 7.50 (m, 2H), 7.40 (m, 3H), 5.00 (q, J=7.5 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 1; 20-26 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 10.9 mg (0.05 mmol) diphenyl disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered, and the filtrate was removed with a rotary evaporator to remove the solvent to obtain the residue, and the residue was separated by a silica gel column. And eluted with the eluent, collect the effluent containing the target product, combine the effluents and concentrate in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, the effluents containing the product were combined, the solvent was distilled off by a rotary evaporator, and the solvent was removed by vacuum drying to obtain a colorless liquid, (1-fluoro-2-phenylvinyl)(phenyl)sulfide, 18.9 mg, with a yield of 82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 2 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 12.3 mg (0.05 mmol) bis(p-tolyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the rotary evaporator distilled off the solvent, vacuum dried to obtain a colorless liquid, (1-fluoro-2-phenylvinyl) (4-methylphenyl) sulfide 19.5 mg, yield Rate 80% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 3 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 13.9 mg (0.05 mmol) bis(4-methylphenyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combine the effluents containing the product, remove the solvent by the rotary evaporator, and dry under vacuum to obtain a colorless liquid, (1-fluoro-2-phenylvinyl)(4-methoxyphenyl)sulfide 21.8 mg, The yield was 84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 4 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 12.4 mg (0.05 mmol) bis(4-aminophenyl) disuflide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the rotary evaporator distilled off the solvent, vacuum dried to obtain a pale yellow liquid, (1-fluoro-2-phenylvinyl) (4-aminophenyl) sulfide 12.5 mg, yield 51%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 5 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 12.7 mg (0.05 mmol) bis(4-fluorophenyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the rotary evaporator distilled the solvent, vacuum dried to obtain a colorless liquid, (1-fluoro-2-phenylvinyl) (4-fluorophenyl) sulfide 18.6 mg, yield 75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 6 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 12.7 mg (0.05 mmol) bis(3-fluorophenyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the rotary evaporator distilled to remove the solvent, vacuum dried to obtain a colorless liquid, (1-fluoro-2-phenylvinyl) (3-fluorophenyl) sulfide 14.9 mg, yield 60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 7 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 12.7 mg (0.05 mmol) bis(2-fluorophenyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluents containing the product, the solvent was distilled off by a rotary evaporator, and dried under vacuum to obtain a pale yellow liquid, (1-fluoro-2-phenylvinyl)(2-fluorophenyl)sulfide 12.9 mg, yield 52%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 8 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 14.3 mg (0.05 mmol) bis(4-chlorophenyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the rotary evaporator distilled off the solvent, vacuum dried to obtain a colorless liquid, (4-chlorophenyl) (1-fluoro-2-phenylvinyl) sulfide 19.3 mg, yield 73%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 9 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 14.3 mg (0.05 mmol) bis(2-chlorophenyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the rotary evaporator distilled off the solvent, vacuum dried to obtain a colorless liquid, (2-chlorophenyl) (1-fluoro-2-phenylvinyl) sulfide 13.3 mg, yield 50%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 10 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 17.7 mg (0.05 mmol) bis(3,5-dichlorphenyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combine the effluents containing the product, remove the solvent by the rotary evaporator, and dry in vacuo to obtain a colorless liquid, (3,5-dichlorophenyl) (1-fluoro-2-phenylvinyl) sulfide 23.0 mg , The yield is 77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 11 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 11.5 mg (0.05 mmol) bis(2-thienyl) disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the solvent was distilled off by a rotary evaporator, and dried under vacuum to obtain a colorless liquid, 16.6 mg of 2-((1-fluoro-2-phenylvinyl)thiophene sulfide, with a yield of 70%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With palladium diacetate; caesium carbonate; triphenylphosphine; zinc In water; N,N-dimethyl-formamide at 80℃; for 12h; | 12 23.8 mg (0.1 mmol) (1-bromo-2,2,2-trifluoroethyl)benzene, 12.3 mg (0.05 mmol) dibenzyl disulfide, 2.2 mg (0.01 mmol) palladium acetate, 26.2 mg (0.1 mmol) triphenylphosphine, 42.4 mg (0.15 mmol) cesium carbonate, 13.0 mg (0.2 mmol) of zinc powder and 14.4 mg (0.8 mmol) of deionized water were added to 2 ml of solvent N,N-dimethylformamide. The reaction was stirred at 80 °C for 12 hours. After the reaction was completed, it was cooled, the mixture was poured into ethyl acetate, and washed with saturated brine (2×15 mL). After extracting the aqueous layer with ethyl acetate, the combined organic layer was dried with anhydrous Na2SO4, filtered and the filtrate was removed from the solvent with a rotary evaporator to obtain the residue. The residue was subjected to column layer separation through a silica gel column and passed through the eluent After washing, the effluent containing the target product is collected, the effluents are combined and concentrated in vacuo to remove the solvent to obtain the target product. The residue is eluted with petroleum ether eluent through a silica gel column, and the effluent is collected according to the actual gradient. TLC detection, combined the effluent containing the product, the rotary evaporator distilled to remove the solvent, vacuum dried to obtain a colorless liquid, benzyl (1-fluoro-2-phenylvinyl) sulfide 11.4 mg, a yield of 47%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (1,2-dimethoxyethane)dichloronickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); lithium tert-butoxide In tetrahydrofuran for 12h; Glovebox; Schlenk technique; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (1,2-dimethoxyethane)dichloronickel(II); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); lithium tert-butoxide In tetrahydrofuran for 12h; Glovebox; Schlenk technique; enantioselective reaction; |