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CAS No. : | 426-58-4 | MDL No. : | MFCD00159083 |
Formula : | C7H5F3O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UPGBQYFXKAKWQC-UHFFFAOYSA-N |
M.W : | 210.17 | Pubchem ID : | 555605 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
100% | With sodium periodate In dichloromethane; water; acetonitrile at 20℃; for 1.58333h; | 2 Ruthenium trioxide (13.9 mg, 0.07 mmol) was added in one portion to a stirred solution of phenyltrifluoromethylsulfide (1.4 ml, 9.8 mmol) in water: dichloromethane: acetonitrile (2: 1: 1; 80 ml) at room temperature. Sodium periodate (6.42 g, 0.03 mol) was then added over 5 min and the resulting mixture stirred at room temperature for 90 minutes. The mixture was then diluted with'butyl methyl ether (250 ml) and water (250 ml) and the organic layer separated and washed sequentially with a saturated solution of sodium bicarbonate (2 x 100 ml) and then brine (100 ml). The organic extract was dried over sodium sulfate, filtered through a plug of silica and then concentrated in vacuo to give the trifluoromethyl sulfone (2.06 g, 100%). The product was used directly in the next step. |
97.5% | With sodium tungstate (VI) dihydrate; dihydrogen peroxide In water; acetonitrile at 50℃; | 1; 8-40; 1-3 Example 1 Control temperature is 15 ~ 25 , prepare the following materials respectively:That is, trifluoromethyl phenyl sulfide (A, 30 g, 0.168 mol) was dissolved in acetonitrile (270 mL) and stirred for clarification, and recorded as material 1;Dissolve Na2WO4 · 2H2O (5.10 g, 0.015 mol) in distilled water (5.4 mL), stir and clarify, and record as material 2;Take 35% H2O2 (81.62 g, 0.84 mol) as material 3;The continuous coil retention volume was 100 mL, and the retention time of the control reaction system in the coil was 60 min.Before punching, first control the coil temperature at 50 , and use the plunger pump to continuously drive the above materials 1, 2 and 3 into the coil respectively in proportion.The material feed rate of material 1 is 4.06 g / min, the material feed rate of material 2 is 0.18 g / min, and the material feed rate of material 3 is 1.36 g / min.Three materials are fed at the same time, the outlet is sampled and the reaction is tracked by HPLC. After the beating, the system in the coil was replaced with pure acetonitrile at the same flow rate as described above.After the temperature of the outflow system was cooled to room temperature, the temperature was controlled at 15-25 , and a 10% sodium sulfite aqueous solution was added to the system to quench it.Then extracted with methyl tert-butyl ether and concentrated to obtain the product trifluoromethyl phenyl sulfone, denoted as B,The internal standard content was 95.0%, and the yield was 97.0%. |
96% | With chromium(VI) oxide; periodic acid In acetonitrile at 20℃; for 2.5h; |
95% | With dihydrogen peroxide; trifluoroacetic acid In water at 60℃; for 3h; | |
91% | With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 1h; Ambient temperature; | |
77% | With dihydrogen peroxide; acetic acid at 40℃; for 5h; | |
65% | With sodium periodate; rhodium(III) chloride hydrate In tetrachloromethane; water; acetonitrile at 20℃; for 1h; Inert atmosphere; | 3 2.3 ((Trifluoromethyl)sulfonyl)benzene (1) [27] To a stirring mixture of Ph-SCF3 3 (2.32 g, 13.0 mmol) in H2O-MeCN-CCl4 (16.0 mL, 2:1:1) was added RuCl3·xH2O (135 mg, 0.65 mmol) at rt, and the mixture was stirred for 5 min. NaIO4 (8.34 g, 39.0 mmol) was added to the mixture, and the mixture was stirred at rt for 1 h. The reaction mixture was diluted with Et2O and filtered through the Celite. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give phenyl triflone 1 (1.80 g, 65%) as yellowish oil. 1H NMR (300 MHz, CDCl3) δ: 8.06 (d, J = 8.1 Hz, 2H), 7.86 (t, J = 8.3 Hz, 1H), 7.72-7.67 (m, 2H) ppm; 19F NMR (282 MHz, CDCl3) δ: -78.9 (s, 3H) ppm; 13C NMR (150.9 MHz, CDCl3) δ: 119.7 (q, J = 325.8 Hz), 129.9, 130.7, 131.3, 136.6 ppm; IR (KBr): 1369, 1219, 1142, 1074, 771, 721, 685, 603 cm-1; HRMS (EI) m/z: calcd for C7H5O2F3S [M]+ 209.9962, Found: 209.9991. |
With chromium(VI) oxide; sulfuric acid at 100 - 130℃; | ||
With chromium(VI) oxide In sulfuric acid | ||
With chromium(VI) oxide; sulfuric acid at 100 - 130℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In benzene at 60℃; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 3% 2: 90% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane 1.) 0 deg C, 10 h, 2.) room temperature, 1 h; | |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 12h; Ambient temperature; Yield given. Yields of byproduct given; | ||
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 10h; Inert atmosphere; Overall yield = 1.08 g; |
With dihydrogen peroxide; ortho-tungstic acid In water at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: (trifluoromethylsulfonyl)benzene With magnesium In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: triethylsilyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.3h; | |
With magnesium In N,N-dimethyl-formamide | 2 Preparation of (trifluoromethyl)triethylsilane (15) Example 2 Preparation of (trifluoromethyl)triethylsilane (15) Into a flame-dried Schlenk flask containing 1.03 g (43 mmol) magnesium turnings and 30 mL DMF under argon, was added 3.0 g (14 mmol) of trifluoromethyl phenyl sulfone (1) at 0° C. After stirring for 5 minutes, 6.45 g (43 mmol) triethylsilyl chloride was added dropwise via syringe. The color of the reaction mixture slowly turned yellow. The progress of the reaction was monitored by 19F NMR periodically. After 1 h, the mixture was slowly warmed to room temperature over 20 minutes period and the reaction mixture was washed with 50 mL ice water. After removing the excess Mg, the solution was extracted with pentane (30 mL*3). The pentane phase was washed carefully with cold 98% sulfuric acid (30 mL*4) to remove most of the siloxane and silanol. Subsequently, the organic phase was washed with cold water (30 mL*2), saturated aqueous NaHCO3 solution (30 mL*2), water (20 mL*2) and dried over anhydrous magnesium sulfate. The solvent was removed under vacuum (~100 Torr), and the resulting crude product also contains PhSSPh as a byproduct (characterized by both GC-MS and NMR). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - -20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - 20℃; | |
85% | With potassium <i>tert</i>-butylate In DMF (N,N-dimethyl-formamide) at -50 - 20℃; for 1h; | 1 Example 1: Preparation of 4-Methyl-a-phenyl-a- (trifluoromethyl) benzenemethanol Into a dry Schlenk flask under an argon atmosphere, was added 7 ML DMF solution of phenyl trifluoromethyl sulfone (LA, 420 mg, 2 mmol) and 4-methylbenzophenone (196 mg, 1 mmol) AT-50C, was added 3 mL DMF solution OF TBUOK (280 mg, 2.5 mmol). The reaction flask was then sealed and the reaction mixture was then stirred FROM-50C for Ih, followed by stirring at-50C to room temperature overnight. The reaction mixture was quenched with 10 mL of ice water, and extracted with ether (20 ml x 3). The combined ether phase was washed with saturated NH4CI aqueous solution, followed by washing with water. After drying over MGSO, the ether solvent was removed under vacuum. The crude product was further purified by column chromatography (hexanes/ether = 9/1) to give 225 mg of product, 4-methyl-a-phenyl-a- (trifluoromethyl) benzenemethanol as a colorless oily liquid, yield 85 %. 1H NMR (CDC13) : 6 2.36 (s, 3H); 2.89 (s, 1H) ; 7.17-7. 51 (m, 9H). 19F NMR (CDC13) : 5-74. 4. MS: 266 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - 20℃; | |
55% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -15 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -50 - 20℃; | |
72% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -15 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -30 - 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With chlorosulfonic acid at 120℃; for 8h; | 2 A solution of trifluoromethylsulfonyl-benzene (596 mg, 2.84 mmol) and chlorosulfonic acid (1.2 ml, 18. 1 mmol) was heated at 120 °C for 8 hours. The mixture was then cooled to room temperature and poured into ice water (50 ml) and extracted into dichloromethane (3 x 50 ml). The organic extracts were dried and concentrated in vacua to give the sulfonyl chloride (711 mg, 81 %). The product was used directly in the next step |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -15 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -15 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -15 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -15 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: (trifluoromethylsulfonyl)benzene; N-<(2,4-dichlorophenyl)methylene>benzamine With potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -70 - -60℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran; N,N-dimethyl-formamide at -70 - -60℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 1,10-Phenanthroline; tetrabutyl ammonium fluoride; copper(II) trifluoroacetate In dimethyl sulfoxide at 130℃; for 8h; Inert atmosphere; Sealed tube; | 4.2 General procedure for the copper-catalyzed trifluoromethylation of arylsulfinate salts General procedure: In a glovebox, arylsulfinate salts (0.50 mmol), [Cu] (0.10 mmol), phen (0.20 mmol), Bu4NF (0.25 mmol), and electrophilic trifluoromethylating reagent (1.25 mmol) were added to an oven-dried resealable Schlenk tube possessing a Teflon screw valve. Freshly distilled DMSO (10.0 mL) was added into this tube and the tube was sealed. The solution was stirred in a preheated (130 °C) oil bath for 8 h. The reaction mixture was then allowed to cool to room temperature and passed through a short silica gel pad to remove metal salts. Water (10.0 mL) was added to the mixture at 0 °C. The resulting mixture was extracted with diethyl ether (6.0 mL×2), and the combined organic layers were washed with water (6.0 mL×2), and then dried over magnesium sulfate. The solvent was removed by rotary evaporation in an ice bath and the resulting product was purified by column chromatography on silica gel with pentane. |
In dimethyl sulfoxide at 25℃; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3.5h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With magnesium; mercury dichloride In N,N-dimethyl-formamide at -50 - 20℃; for 3h; Inert atmosphere; Green chemistry; | Typical procedure for nucleophilic trifluoromethylation of arylidenemalononitriles General procedure: A mixture of sulfone 5 (420 mg, 2 mmol) and arylidenemalononitrile 10 (154 mg, 1 mmol) in freshly distilleddimethylformamide (DMF) (3 mL) was added drop-wise to a mixture of HgCl2 (16 mg, 0.06 mmol) and unactivated Magnesium turnings (49 mg, 2 mmol) in DMF at -50 °C. The reaction was stirred and allowed to warm to rt after which stirring was continued for 3 h. The reaction was quenched with 3MHCl, diluted with water and extracted (3) with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4 and concentrated.The crude product was purified by column chromatography (20% ethyl acetate in hexanes) to get 11 as a pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper(I) oxide In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; | 12 Under an argon atmosphere, mesityl trifluoromethanesulfonic acid (phenyl) iodonium (142mg, 300μmol), trifluoromethanesulfinate sodium fin acid (70.2mg, 450μmol) and copper oxide (I) (2.1mg, 15μmol) of N, N- dimethyl after stirring formamide (1.5 mL) solution at room temperature for 3 days, 0 ° and cooled to C was added a saturated aqueous sodium hydrogen carbonate solution, mixing the aqueous layer the solvent (hexane: ethyl acetate = 1: 1) and extracted with. The obtained organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 50: 1) to give the (trifluoromethylsulfonyl) benzene (38.8mg, 184μmol, 61%) as a colorless oily substance |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 48% 2: 30% | With copper(I) oxide In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; | 29 Under an argon atmosphere, N, N-dimethylformamide (1 .5ML) solution of [4-(methoxycarbonyl)phenyl](phenyl)iodonium trifluoromethanesulfonate(129mg, 300μmol), Trifluoromethanesulfinic Acid Sodium(70.2mg, 450μmol) and copper oxide (I) (2.1mg, 15μmol) was stirred for 3 daysat room temperature, and then cooled to 0 ° C and saturated aqueous sodiumhydrogen carbonate solution was added, and the aqueous layer was extracted withmixed solvent (hexane: ethyl acetate = 1: 1). The obtained organic layer waswashed with saturated brine, dried over sodium sulfate, and concentrated underreduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1-3: 1) to give, H-NMR and F-NMR from 4- (trifluoromethylsulfonyl ) benzoate (yield: 48%) and (trifluoromethyl) benzene (yield: confirmed the production of 30%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper(I) oxide In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; | 1 Under an argon atmosphere, N, N-dimethylformamide (1 .5ML)solution of trifluoromethanesulfonic acid diphenyliodonium (129mg, 300μmol),Trifluoromethanesulfinic Acid Sodium (70.2mg, 450μmol) and copper oxide (I)(2.1mg, 15μmol) was stirred for 3 days at room temperature, and then cooled to 0 ° C and saturated aqueous sodium hydrogen carbonate solution was added, andthe aqueous layer was extracted with mixed solvent (hexane: ethyl acetate = 1:1). The obtained organic layer was washed with saturated brine, dried oversodium sulfate, and concentrated under reduced pressure. The resulting crudeproduct was purified by silica gel column chromatography (hexane: ethyl acetate= 50: 1) to give (trifluoromethylsulfonyl) benzene (39.8mg, 189μmol, 63%) as acolorless oily substance. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; | 30 Example 30 2, 8-Difluoro-S- (trifluoromethyl) dibenzothiophenium trifluoromethanesulfonate (1.0 mmol) was added to a stirred solution of sodium benzenesulfinate (1.0 mmol) and 4-chlorobenzotrifluoride (1.0 mmol) in 5 mL of dimethylsulfoxide (DMSO) at room temperature under nitrogen atmosphere and the mixture was stirred for 1 h. 4-Chlorobenzotrifluoride was a reference for 19F NMR analysis. The 19F NMR analysis of the reaction mixture showed that phenyl trifluoromethyl sulfone was produced in 70yield. The product was isolated by the standard post-treatment and identified by spectral analysis: 19F NMR (376.6 MHz, CDCl3) δ -78.50 ppm (s, CF3) . |
70% | In N,N-dimethyl-formamide Inert atmosphere; | |
70% | In N,N-dimethyl-formamide at 20℃; for 1h; | 12 Perfluoroalkylation of organic compounds with S-(perfluoroalkyl)-dibenzothiophene trifluoromethanesulfonate (I)The perfluoroalkylation of other organic compounds can be performed with reference to the following general steps. Chemical test usedThe agents, reaction conditions and reaction results are listed in Table 2 below |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 6 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With bromine In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 7 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 8 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #3: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; hexane Inert atmosphere; | 10 2.10 2-((Trifluoromethyl)sulfonyl)phenol (2f) [29] To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. 2.5 1-Methyl-2-((trifluoromethyl)sulfonyl)benzene (2a) [ 27 ] According to the general procedure, 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL), n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol), phenyltriflone 1 (210mg, 1.00mmol) and methyl iodide (124μL, 2.00mmol) gave the title compound (165mg, 73%) as colorless oil. 1H NMR (300MHz, CDCl3) δ: 8.08 (d, J=8.1Hz, 1H), 7.68 (t, J=7.2Hz, 1H), 7.49-7.42 (m, 2H), 2.72 (s, 3F) ppm; 19F NMR (282MHz, CDCl3) δ: -78.8 (s, 3H) ppm; 13C NMR (150.9MHz, CDCl3) δ: 20.6, 120.1 (q, J=326.7Hz), 127.2, 129.7, 133.3, 133.6, 136.4, 142.2ppm; IR (KBr): 1363, 1203, 1145, 1122, 1057, 1043, 758, 690, 607cm-1; HRMS (EI) m/z: calcd for C8H7O2F3S [M]+ 224.0119, Found: 224.0143. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 5 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. 2.5 1-Methyl-2-((trifluoromethyl)sulfonyl)benzene (2a) [ 27 ] According to the general procedure, 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL), n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol), phenyltriflone 1 (210mg, 1.00mmol) and methyl iodide (124μL, 2.00mmol) gave the title compound (165mg, 73%) as colorless oil. 1H NMR (300MHz, CDCl3) δ: 8.08 (d, J=8.1Hz, 1H), 7.68 (t, J=7.2Hz, 1H), 7.49-7.42 (m, 2H), 2.72 (s, 3F) ppm; 19F NMR (282MHz, CDCl3) δ: -78.8 (s, 3H) ppm; 13C NMR (150.9MHz, CDCl3) δ: 20.6, 120.1 (q, J=326.7Hz), 127.2, 129.7, 133.3, 133.6, 136.4, 142.2ppm; IR (KBr): 1363, 1203, 1145, 1122, 1057, 1043, 758, 690, 607cm-1; HRMS (EI) m/z: calcd for C8H7O2F3S [M]+ 224.0119, Found: 224.0143. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 11 2.11 (2-((Trifluoromethyl)sulfonyl)phenyl)boronic acid (2g) To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added 50 n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. 64 (MeO)3B (223μL, 2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. 3.0M 65 NaOH and 30% 66 H2O2 were added to the mixture. The reaction mixture was neutralized with 1M HCl and extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound 3f (117mg, 52%) as a yellow solid. 1H NMR (300MHz, CDCl3) δ: 7.76-7.70 (m, 2H), 7.16-7.11 (m, 2H) ppm; 19F NMR (282MHz, CDCl3) δ:-79.8 (s, 3F) ppm; 13C NMR (150.9MHz, CDCl3) δ: 112.9, 119.7, 119.8 (q, J=325.6Hz), 121.3, 131.5, 139.8, 158.9ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 12 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 13 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: ethyl cyanoformate In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 14 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: (trifluoromethylsulfonyl)benzene With n-butyllithium; benzoyl chloride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: benzoyl chloride In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 16 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 9 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: (trifluoromethylsulfonyl)benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 15 General procedure of ortho-lithiation and addition General procedure: To a stirring mixture of 2,2,6,6-tetramethylpiperidine (255μL, 1.50mmol) in dry THF (5.0mL) was added n-BuLi (1.30M solution in hexane, 1.15mL, 1.50mmol) at-78°C, and the mixture was stirred at 0°C for 30min. The mixture was cooled to-78°C, phenyltriflone 1 (210mg, 1.00mmol) was slowly added to the mixture, and the mixture was stirred at-78°C for 2h. Electrophile (2.00mmol) was added to the mixture and the mixture was stirred at-78°C for overnight. H2O was added at rt and the mixture was diluted with Et2O. The organic layer was separated and the aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give ortho-substituted phenyl triflone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C38H54Cl2N4Pd; lithium tert-butoxide In tetrahydrofuran at 70℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C38H54Cl2N4Pd; lithium tert-butoxide In tetrahydrofuran at 70℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C38H54Cl2N4Pd; lithium tert-butoxide In tetrahydrofuran at 70℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium hydroxide monohydrate; C38H54Cl2N4Pd In tetrahydrofuran at 70℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28 %Spectr. | With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C38H54Cl2N4Pd; lithium tert-butoxide In tetrahydrofuran at 70℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tris-(dibenzylideneacetone)dipalladium(0); copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 80℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry; | |
81% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 0.0833333h; Microwave irradiation; | 3.2. General Procedure for the Sonogashira CouplingReaction General procedure: Aryl halide (1.5 mmol), alkyne (1.8 mmol, 1.2 equiv),Pd(PPh3)2Cl2 (53 mg, 0.075 mmol, 0.05 equiv) and Et3N(666 mg, 6 mmol, 4 equiv) were added to 10 mL microwave vial containing 4 mL [BMIm][BF4]. The mixture was irradiatedin a microwave reactor at 80 °C for 5 minutes. Completionof the reaction was confirmed by TLC. Then the mixturewas extracted with hexane (4 x 10 mL) and the organic layerswere combined. The solvent was removed by an evaporatorand the residue was purified by flash column chromatographyto afford the corresponding product. The ionic liquidcontaining catalyst was washed with water (3 x 5mL) thenwas placed in a high vacuo system to remove water residue.The ionic liquid was used for the next cycle without furtherpurification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With Cs2CO3 In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Inert atmosphere; Irradiation; |
Tags: 426-58-4 synthesis path| 426-58-4 SDS| 426-58-4 COA| 426-58-4 purity| 426-58-4 application| 426-58-4 NMR| 426-58-4 COA| 426-58-4 structure
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Precautionary Statements-General | |
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P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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