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CAS No. : | 53136-21-3 | MDL No. : | MFCD00028019 |
Formula : | C13H11BrS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XNMPJRAVZAWQMD-UHFFFAOYSA-N |
M.W : | 279.20 | Pubchem ID : | 4191541 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 70.35 |
TPSA : | 25.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.72 cm/s |
Log Po/w (iLOGP) : | 2.96 |
Log Po/w (XLOGP3) : | 4.62 |
Log Po/w (WLOGP) : | 4.59 |
Log Po/w (MLOGP) : | 5.08 |
Log Po/w (SILICOS-IT) : | 4.63 |
Consensus Log Po/w : | 4.37 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.88 |
Solubility : | 0.00372 mg/ml ; 0.0000133 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.88 |
Solubility : | 0.00371 mg/ml ; 0.0000133 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.28 |
Solubility : | 0.000147 mg/ml ; 0.000000526 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.26 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P201-P264-P280-P301+P330+P331-P312 | UN#: | 3077 |
Hazard Statements: | H302-H361-H372-H410 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 |
---|---|---|
99% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 23℃; for 5h; | |
98% | With dihydrogen peroxide In ethanol at 50℃; for 0.85h; | |
97% | With aluminium trichloride; 3-carboxypyridinium chlorochromate In acetonitrile for 0.0416667h; microwave irradiation; |
97% | With dihydrogen peroxide In acetonitrile at 25℃; for 0.133333h; | General procedure for the preparation of sulfones General procedure: To a mixture of sulfide (1 mmol) and AgCeO2 (0.05 g) in2 cm3acetonitrile, 0.3 cm330% H2O2(3 equiv.) was added,and the mixture was stirred at room temperature until thecomplete consumption of sulfide (monitored by TLC). Aftercompletion of the reaction, 10 cm3acetonitrile was addedto the reaction mixture and the mixture heated for 10 minat 50 °C. After that, the catalyst was separated from thereaction mixture by filtration and the organic residue wasextracted with 20 cm3EtOAc, washed with 10 cm3distilledwater, dried over MgSO4,and recrystallized in a mixture ofEtOH and H2Oto obtain the pure product. |
96% | With aluminium trichloride; butyltriphenylphosphonium dichromate In acetonitrile for 0.05h; microwave irradiation; | |
With dihydrogen peroxide; acetic acid | ||
Multi-step reaction with 2 steps 1: Oxone(R) / acetone; H2O / 0 °C 2: vanadyl acetylacetonate; (S)-C13H17I2NO2; H2O2 / CH2Cl2; H2O / 1.67 h / 20 °C | ||
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 4h; | Preparation of 1-(Benzylsulfonyl)-4-bromobenzene (8e) To a solution of 7e (0.131 g, 0.469 mmol) in DCM (2 mL) was added 3-chloroperoxybenzoic acid (0.231 g, 77% w/v, 1.03 mmol). The resulting mixture was stirred for 4 h at r.t. The reaction mixture was then basified with 1 N NaOH (5 mL) and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resultant white solid (0.115 g, 79% yield) was used in the next step without further purification. 1H NMR (400 MHz, Methanol-d4) δ ppm 4.5 (s, 2H), 7.11-7.15 (m, 2H), 7.24-7.35 (m, 2H), 7.54 (d, J = 8.8 Hz, 2H), 7.70 (d, J = 8.8 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With dihydrogen peroxide; nitric acid In ethanol at 25℃; for 0.3h; chemoselective reaction; | |
97% | With basolite C300; dihydrogen peroxide In acetonitrile at 30℃; for 1h; Green chemistry; | |
96% | With dihydrogen peroxide In ethanol at 50℃; for 0.233333h; |
96% | With dihydrogen peroxide; trichlorophosphate In diethyl ether at 0℃; for 0.166667h; | |
95% | With aluminium trichloride; butyltriphenylphosphonium dichromate In acetonitrile for 0.0416667h; microwave irradiation; | |
95% | With trifluoromethylsulfonic anhydride; dihydrogen peroxide In ethanol at 20℃; for 0.25h; | |
95% | With urea hydrogen peroxide adduct In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry; | 2.3 General procedure for the oxidation reactions catalyzed by UHP/SSA General procedure: The solid reaction mixture containing the sulfide (1mmol), UHP (2mmol) and SSA (0.1g) were thoroughly mixed and the resulting mixture was stirred magnetically. The progress of the reaction was followed by TLC (eluent: n-hexane/ethyl acetate: 2:1). After completion of the reaction, CHCl3 (20mL) was added and the solid catalyst was removed by filtration. The filtrate was washed with water (15mL) and the extract was dried over MgSO4. After evaporation of the solvent, the crude product was purified by chromatography on silica gel (25-30mesh), eluting with ethyl acetate/n-hexane to give pure sulfoxides. |
94% | With iron(III) chloride; urea hydrogen peroxide adduct In acetonitrile at 20℃; for 2.5h; Green chemistry; | 2.2 General Procedure: Oxidation Reactions CatalyzedbyUHP/FeCl3 System inCH3CNasSolvent General procedure: In a 25 round-bottomed flask, to a solution a sulfide(1mmol) in CH3CN(10mL), UHP (1.5mmol) and FeCl3(1 mmol) were added successively and the mixture wasstirred magnetically at room temperature. The reaction progresswas followed by TLC (eluent: n-hexane/ethyl acetate:2:1). After completion of the reaction, the solvent wasremoved under vacuum and the residue was quenched byadding water (15mL), extracted with CH2Cl2(3 × 10mL).The combined organic layers were washed with water,dried over MgSO4and the solvent was removed in vacuum.The residue was purified by chromatography on silica gel(25-30 mesh), eluting with ethyl acetate/n-hexane to givepure sulfoxides. |
93% | With aluminium trichloride; 3-carboxypyridinium chlorochromate In acetonitrile for 0.0333333h; microwave irradiation; | |
92% | With dihydrogen peroxide In acetonitrile at 20℃; for 0.75h; Green chemistry; chemoselective reaction; | |
90% | With dihydrogen peroxide In ethanol at 20℃; for 0.75h; Green chemistry; | General procedure for the oxidation of sulfides to the sulfoxides General procedure: The catalyst (0.010 g) was added to solution of sulfide (1 mmol) and H2O2 (0.5 mL) in ethanol (2 mL). The reaction mixture was stirred at room temperature, and the progress of the reaction was monitored by TLC (acetone:n-hexane, 2:8). After completion of the reaction, catalyst was separated by an external magnet and washed with ethyl acetate; next, the product was extracted with ethyl acetate (5 mL 9 4). The organic layer was dried over anhydrous Na2SO4 (1.5 g). Finally, the organic solvents were evaporated, and the corresponding sulfoxides were obtained in high to excellent yields (88-99%). |
89% | With water; benzyltriphenylphosphonium tribromide In acetonitrile Reflux; chemoselective reaction; | |
83% | With 18-crown-6 ether; N-carbo-(-)-menthoxy-4-tolylsulfonimidoyl chloride In acetonitrile at 0 - 4℃; for 4h; | |
With dihydrogen peroxide; acetic acid | ||
With oxone In water; acetone at 0℃; | ||
95 %Chromat. | With 2,2,2-trifluoroethanol; dihydrogen peroxide at 20℃; for 0.5h; Green chemistry; | 2.2. General procedure for the oxidation of sulfides to sulfoxides General procedure: In a round-bottomed flask (25 mL) equippedwith a magnetic stirrer,sulfide (1 mmol) was added to a reaction flask in the presence of4 mmol H2O2 (30%) and 0.02 g SBA-15 in 3 mL TFE and stirred atroom temperature for an appropriate time (Table 1). After completionof the reaction, TFE was separated from reaction mixture at 80 °C andreused for the next reactions. Then, the product was extracted from reactionmixturewith chloroformand then the final productwas obtainedby evaporating chloroform from sulfoxide (Fig. 4). |
With sodium periodate In ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: para-bromobenzenethiol With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; | |
With sodium hydroxide | ||
With potassium carbonate In acetone Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium; ethylene dibromide 1.) THF, reflux, 1 h, 2.) 3 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate In acetone for 24h; Reflux; | |
84% | With potassium carbonate In acetone for 24h; Reflux; | |
80% | at 100℃; for 8h; Neat (no solvent); |
76% | Stage #1: para-bromobenzenethiol With sodium hydride; potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | |
66.7% | With sodium hydride In N,N-dimethyl-formamide; paraffin at 50 - 60℃; for 1h; | |
51% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4h; | Preparation of Benzyl(4-bromophenyl)sulfane (7e) To a solution of 6 (0.15 g, 0.793 mmol) in THF (2 mL) was added DIEA (0.154 g, 1.19 mmol) followed by benzyl bromide (0.204 g, 1.19 mmol) and the mixture stirred for 4 h at r.t. The reaction mixture was diluted with water (40 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. Purification of the resultant residue by column chromatography (eluant; hexane) provided the title compound (0.131 g, 51% yield) as a white solid. 1H NMR (400 MHz, Methanol-d4) ppm 3.16 (m, 2H), 7.17-7.29 (m, 7H), 7.38 (d, J = 7 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; potassium bromide; copper(I) bromide at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 41 % Chromat. 2: 15 % Chromat. | With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 85% 2: 5% | Stage #1: 1-benzylsulphanyl-4-bromobenzene With titanium(IV) isopropylate; (S,S)-hydrobenzoin In hexane at 20℃; for 0.5h; Stage #2: With tert.-butylhydroperoxide In hexane at 20℃; for 48h; Further stages.; | |
1: 58% 2: 25% | With titanium(IV) isopropylate; di-tert-butyl peroxide; (1R,2R)-1,2-dicyclohexyl-1,2-ethanediol In hexane; water at 20℃; for 48h; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With chiral Schiff base derived from (R)-BINOL and (S)-t-leucinol; dihydrogen peroxide In dichloromethane at 0℃; for 24h; | |
84% | Stage #1: 1-benzylsulphanyl-4-bromobenzene With titanium(IV) isopropylate; (S,S)-hydrobenzoin In hexane at 20℃; for 0.5h; Stage #2: With tert.-butylhydroperoxide In hexane at 20℃; for 48h; Further stages.; | |
Multi-step reaction with 2 steps 1: Oxone(R) / acetone; H2O / 0 °C 2: 31 percent / vanadyl acetylacetonate; (S)-C13H17I2NO2; H2O2 / CH2Cl2; H2O / 1.67 h / 20 °C |
With titanium(IV) isopropylate; tert.-butylhydroperoxide; (R,R)-hydroxybenzoin In hexane optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: With sulfur In tetrahydrofuran; hexane at -78℃; Stage #3: benzyl bromide In tetrahydrofuran; hexane at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With samarium In methanol at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 24h; | |
56% | With 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride; potassium <i>tert</i>-butylate; nickel diacetate In N,N-dimethyl-formamide at 110℃; for 6h; Glovebox; Inert atmosphere; | General procedure for the coupling reaction of aryl halides with phenyl sulfide ; Benzyl 4-bromophenyl sulfide General procedure: In a typical run, a 5 mL vial equipped with a magnetic bar was charged with a mixture of aryl halide (1 mmol), thiol (1 mmol), Ni(OAc)2 (0.1 mmol), NHC (0.05 mmol) and KOtBu (1.5 mmol) in glove box, 2 mL of DMF was injected, the mixture was stirred at 70 °C for 12 h. After cooling to room temperature, brine was added to the reaction mixture, and the aqueous phase was extracted with dichloromethane for three times. The combined organic layers were dried with Mg2SO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel to afford the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With (S)-C13H17I2NO2; vanadyl acetylacetonate; dihydrogen peroxide In dichloromethane; water at 20℃; for 16h; | |
41% | With (S)-(-)-2-(N-3,5-diiodosalicylidene)amino-3,3-dimethyl-1-butanol; dihydrogen peroxide In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; sodium iodide In dichloromethane at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1S,2R,3R,4R)-2-OOH-2-(2'-furyl)-3-MeOCH2-bicyclo-heptane In toluene at -20℃; Title compound not separated from byproducts.; | ||
1: 36 %Chromat. 2: 5 %Chromat. | With titanium(IV) isopropylate; di-tert-butyl peroxide; (S,S)-hydrobenzoin In hexane; water at 20℃; for 1.25h; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With bromine; triphenylphosphine; copper(I) bromide In acetonitrile for 26h; Heating; | |
96% | With trifluoromethylsulfonic anhydride; potassium iodide In acetonitrile at 20℃; for 0.05h; | |
93% | With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; triphenylphosphine In dichloromethane at 20℃; for 0.0166667h; | 2.1 General procedure for synthesis of pyrimidine General procedure: To a mixture of TBBDA (0.4 mmol) and PPh3 (2.5 mmol)in CH2Cl2 (5 mL), sulfoxide (1 mmol) was added at roomtemperature. The progress of the reaction was monitoredby TLC. After completion of the reaction (Table 2), thesolvent was evaporated. The crude product was purified byshort column chromatography (packed with silica gel,using n-hexane/ethyl acetate (8:2) as the eluent) toachieve the desired sulfide with good to excellent yields |
87% | With hydrogenchloride; N-Bromosuccinimide In 1,4-dioxane at 120℃; for 10h; Schlenk technique; Sealed tube; | 2 General procedure for synthesis of compounds 2 General procedure: Under an air atmosphere,a 10 mL of Schlenk tube equipped with a stir bar was charged with sulfoxide(0.2 mmol), NBS (0.2 equiv), HCl (2.0 equiv, 12 M) and 1,4-dioxane(2.0 mL). The tube was sealed with a Teflon lined cap. The reaction mixturewas stirred at 120 °C for 10 h in oil bath. After the completion ofthe reaction, saturated NaOH (2 mL) was added to the mixture, and extractedwith ethyl acetate (4 mL × 3). The combined organic extracts were dried over anhydrous Na2SO4. Subsequently, the solvent was filtered and evaporated under reduced pressure, and theresidue was purified by flash column chromatography on silica gel withpetroleum as the eluent to give the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) Mg, BrCH2CH2Br / 1.) THF, reflux, 1 h, 2.) 3 h 2: 87 percent / 33percent H2O2 / acetic acid / 1.5 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) Mg, BrCH2CH2Br / 1.) THF, reflux, 1 h, 2.) 3 h 2: 87 percent / 33percent H2O2 / acetic acid / 1.5 h / 70 °C 3: 87 percent / SOCl2 / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With N-Bromosuccinimide; potassium <i>tert</i>-butylate In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 15h; Inert atmosphere; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium(IV) isopropylate; tert.-butylhydroperoxide; (S,S)-hydrobenzoin In hexane optical yield given as %ee; enantioselective reaction; | ||
72 %Chromat. | With titanium(IV) isopropylate; di-tert-butyl peroxide; (S,S)-hydrobenzoin In hexane; water at 20℃; for 29h; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: 1-benzylsulphanyl-4-bromobenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 2h; Stage #2: methyl iodide In tetrahydrofuran; pentane regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 9h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: 1-benzylsulphanyl-4-bromobenzene With tert.-butyl lithium In tetrahydrofuran at -68℃; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran at -68℃; for 1h; Inert atmosphere; Stage #3: chloro-trimethyl-silane Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 1-benzylsulphanyl-4-bromobenzene With tert.-butyl lithium In tetrahydrofuran at -68℃; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran at -68℃; for 1h; Inert atmosphere; Stage #3: N,N-diethylcarbamyl chloride Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: 1-benzylsulphanyl-4-bromobenzene With tert.-butyl lithium In tetrahydrofuran at -68℃; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran at -68℃; for 1h; Inert atmosphere; Stage #3: methyl iodide Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: 1-benzylsulphanyl-4-bromobenzene With tert.-butyl lithium In tetrahydrofuran at -68℃; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran at -68℃; for 1h; Inert atmosphere; Stage #3: Tert-butyl isocyanate Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In 1,2-dichloro-ethane at 80℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With palladium diacetate; silver carbonate In N,N-dimethyl acetamide at 120℃; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: benzyl chloride With [2,2]bipyridinyl; copper(ll) sulfate pentahydrate; sodium thiosulfate pentahydrate In methanol; water at 80℃; for 2h; Schlenk technique; Stage #2: 4-bromo-aniline With tert.-butylnitrite In methanol; water at 0 - 80℃; for 4.66667h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With di-tert-butyl peroxide; iodine In toluene at 120℃; for 5h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: benzyl chloride With [2,2]bipyridinyl; copper(ll) sulfate pentahydrate; Sodium thiosulfate pentahydrate In water at 80℃; for 2h; Schlenk technique; Stage #2: 1-(4-bromophenyl)-2-(pyrrolidin-1-yl)diazene With boron trifluoride diethyl etherate In water at 20℃; for 12h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: 4-bromo-aniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; Stage #2: benzyl thiosulphate With tris(bipyridine)ruthenium(II) dichloride hexahydrate; potassium carbonate In water; dimethyl sulfoxide at 20℃; for 5h; Schlenk technique; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane In 1,2-dichloro-ethane at 80℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With [bis(acetoxy)iodo]benzene; ammonium acetate In ethanol at 20℃; for 2h; | 12 Embodiment 12 The thioether (279 mg, 1.0 µM), iodobenzene diacetate (966 mg, 3.0 µM), ammonium acetate (308 mg, 4.0 µM) containing ethanol is added 10 ml bottle of the reaction, the reaction at room temperature for two hours. After the reaction is finished to remove the solvent, column chromatography treatment, to obtain the product of 279 mg, yield 90%. |
76% | With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 3h; chemoselective reaction; | |
76% | With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With para-bromobenzenethiol In tetrahydrofuran at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hydride; lithium iodide In tetrahydrofuran; mineral oil at 50℃; for 8h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With tris(bipyridine)ruthenium(II) dichloride hexahydrate; potassium carbonate In water; dimethyl sulfoxide at 20℃; for 5h; Irradiation; Inert atmosphere; | 5 Example 5 Synthesis of benzyl (4-bromophenyl) sulfide In the evacuated reaction tube, Ru (bpy) 3Cl2 6H2O (2.9 mg, 4 * 10-3 mmol), substrate 7a (54.9 mg, 0.2 mmol) Substrate 2 (226.0 mg, 1 mmol), K2CO3 (55.3 mg, 0.4 mmol), DMSO (containing 50 eq H2O) (about 0.78 mL DMSO / 0.22 mL H2O) (1 mL) was added and the reaction was stirred at room temperature for 5 hours under the irradiation of a 8 W compact energy-saving lamp to monitor the progress of the reaction. After completion of the reaction, ethyl acetate (10 mL) was added to the system at room temperature, dried over anhydrous magnesium sulfate, filtered, concentrated and chromatographed to give colorless oil 7 (32.7 mg, 59%), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With thiourea In water for 9.3h; Reflux; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With nanolayered cobalt-molybdenum sulphide with Co/(Mo+Co) mole ratio 0.83 In Hexadecane; toluene at 180℃; for 18h; Inert atmosphere; Autoclave; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-benzylsulphanyl-4-bromobenzene With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: 4-((methoxymethoxy)methyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; | 5.1.23. 4-(1-(1,3-Dihydro-1-hydroxy-2,1-benzoxaborole-6-yl)-1-hydroxylmethyl)benzonitrile (38) General procedure: To a solution of i-PrMgCl (0.5 mL, 2.0 M in THF, 1.0 mmol) in anhydrous THF (2 mL), was added n-BuLi (0.8 mL, 2.5 M solution in THF, 2.0 mmol) at 0 C under nitrogen atmosphere. After stirred for 30 min, the solution was cooled to 10 C. A solution of 4-bromobenzonitrile(0.18 g, 1.0 mmol) in THF (2 mL) was added dropwise. After stirred for 0.5 h at 10 C, the solution was cooled to 78 C. Then a solution of compound 10 (0.31 g, 1.0 mmol) in THF (3 mL) was added. After stirred for 0.5 h at 78 C, the reaction was quenched with saturated aqueous NH4Cl (5 mL) and extracted with ethyl acetate (15 mL × 3). The organic phase was combined, dried over anhydrous Na2SO4, and evaporated invacuo followed by purification on silica gel column chromatography(petroleum ether/EtOAc, V/V, 5/1) to obtain compound 16a (0.16 g,39.0%) as a colorless oil. Compound 16a (0.16 g, 0.39 mmol) was dissolved in dioxane (3 mL) and 6 M HCl (3 mL). The reaction was stirred atrt for 12 h. The solution was extracted with ethyl acetate (10 mL × 3).The organic phase was combined, dried over anhydrous Na2SO4, and evaporated in vacuo followed by purification on silica gel column chromatography (DCM/MeOH, V/V, 50/1) to obtain compound 38 as awhite solid (20 mg, 18.8%). 1H NMR (400 MHz, DMSO-d6): δ 9.11 (s,1H), 7.74 (d, J = 8.2 Hz, 2H), 7.68 (s, 1H), 7.57-7.51 (m, 2H), 7.45 (d, J= 7.8 Hz, 1H), 7.31 (d, J = 7.9 Hz, 1H), 6.15 (d, J = 3.9 Hz, 1H), 5.82 (d,J = 3.7 Hz, 1H), 4.91 (s, 2H) ppm; 13C NMR (100 MHz, DMSO-d6): δ153.4, 151.8, 143.8, 132.6, 129.6, 128.9, 127.6, 121.7, 109.9, 74.2,70.2 ppm; HRMS (ESI): [M H] C15H11BNO3 calcd 264.0832, found264.0836; mp: 95-97 C; HPLC: purity 95.1%, retention time 12.9 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 18-crown-6 ether; potassium <i>tert</i>-butylate In toluene at 120℃; for 3h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With dipotassium hydrogenphosphate; 4,4'-Dichlorobenzophenone; 4,4'-di-tert-butyl-2,2'-bipyridine; nickel dichloride at 20℃; for 6h; Irradiation; | 5 Example 5 Combine N-(4-bromophenylthio)succinimide (57mg),Dichlorobenzophenone (10mg),NiCl2(2.2mg),4,4'-di-tert-butyl-2,2'-bipyridine (2.7mg),K2HPO4 (70mg) addedInto the Shrek reaction tube,Finally add toluene (5mL),Placed under two 23W CFL lights,Irradiate the reaction at room temperature for 6h,After the reaction,Extraction, drying, desolventization,Chromatography with column chromatography(Eluent: pure petroleum ether) The target product is isolated and obtained.The target product is a white solid,The yield was 41%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; copper(II) sulfate at 205℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium hydroxide In water; acetonitrile at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With rhodium (II) octanoate dimer In dichloromethane at 0 - 40℃; for 48h; Inert atmosphere; | General Procedure: General procedure: A solution of S1 (1.0 equiv) and Rh 2 (oct) 4 (2.5 mol%) in dry DCM (c = 0.5 M) was stirred at room temperature under argon. After cooling to 0 °C, diazomalonate 1 (S2a/S2b, 1.1 equiv) was added slowly. The reaction mixture was stirred at 40 °C (oil bath) for 24-48 h. Then it was cooled to room temperature and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel or by recrystallization. S1 were synthesized according to reported procedures or commercial available. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium <i>tert</i>-butylate In acetonitrile at 70℃; for 12h; Schlenk technique; Inert atmosphere; | 4.2. General procedure for the cross-coupling of benzylammonium salts with aryl thiophenols General procedure: A Schlenk flask was charged with the required benzylammonium salts (0.40 mmol), aryl thiophenols (0.20 mmol), N-heterocyclic carbene-palladium(II) complex (5 mol%), KtOBu (2.0 equiv), and CH3CN (2.0 mL). The mixture was stirred at 70 °C for 12 h under N2. After cooling, the mixture was evaporated and the product was isolated by preparative TLC on silica gel plates. The analytical data of the catalysis products are given in the Supporting Information. |
77% | With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium <i>tert</i>-butylate In acetonitrile at 70℃; for 12h; Schlenk technique; Inert atmosphere; | 4.2. General procedure for the cross-coupling of benzylammonium salts with aryl thiophenols General procedure: A Schlenk flask was charged with the required benzylammonium salts (0.40 mmol), aryl thiophenols (0.20 mmol), N-heterocyclic carbene-palladium(II) complex (5 mol%), KtOBu (2.0 equiv), and CH3CN (2.0 mL). The mixture was stirred at 70 °C for 12 h under N2. After cooling, the mixture was evaporated and the product was isolated by preparative TLC on silica gel plates. The analytical data of the catalysis products are given in the Supporting Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 90℃; for 12h; Inert atmosphere; |
Tags: 53136-21-3 synthesis path| 53136-21-3 SDS| 53136-21-3 COA| 53136-21-3 purity| 53136-21-3 application| 53136-21-3 NMR| 53136-21-3 COA| 53136-21-3 structure
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