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CAS No. : | 57606-65-2 | MDL No. : | MFCD18974275 |
Formula : | C7H4F4O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LKAKRVBLXMUOHC-UHFFFAOYSA-N |
M.W : | 244.16 | Pubchem ID : | 550560 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 | UN#: | 3265 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
79% | With pyridine In dichloromethane at 0℃; for 6h; Inert atmosphere; | Procedure A. Preparation of aryl trifluoromethanesulfonates General procedure: Prepared following an adaptation of the published procedure.7 To a cooled (0 °C), stirred solution of the phenol (10 mmol) and pyridine (20 mmol) in CH2Cl2 (50 mL) under Ar or N2 was added via syringe trifluoromethanesulfonic anhydride (13 mmol). After stirring for 1-3 h, the reaction mixture was treated with aq sat NH4Cl. The CH2Cl2 phase was washed sequentially with aqueous copper sulfate (2x) and H2O and dried over MgSO4. Filtration, concentration in vacuo and purification afforded the product. |
50% | With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | |
9% | With pyridine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice; | General Procedure A: General synthesis of aryl triflates General procedure: To a flame-dried 25 mL round-bottom flask fitted with a rubber septum and equipped with a magnetic stir bar was added phenol (1.0 equiv). The contents were evacuated and backfilled three times with nitrogen. Anhydrous DCM (0.7 M) and distilled pyridine (4.2 equiv) were added via syringe and the stirred solution was cooled in an ice bath for 10 min. Triflic anhydride (1.4 equiv) was added dropwise over 5 min. The reaction was slowly warmed to room temperature. After 10-14 h, the reaction was diluted with Et2O (30 mL) and quenched with 1 M aqueous HCl (30 mL). The organic layer was extracted. The organic layer washed with water (2 x 25mL), then brine (25 mL), dried over MgSO4, filtered, and concentrated via rotary evaporation. The aryl triflate was purified by flash chromatography (gradient 2-20% EtOAc/hexanes over 45 column volumes. |
(i) aq. NaOH, (ii) /BRN= 1813600/; Multistep reaction; | ||
With triethylamine In toluene at 20℃; Flow reactor; | ||
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Schlenk technique; | ||
With triethylamine In dichloromethane at 0 - 20℃; | 2. General Procedure for Synthesis of Aryl Triflates General procedure: To a solution of phenols (1.0 equiv, 0.5 M) in CH2Cl2 was added Et3N (2 equiv) at 0 °C. The mixture was allowed to stirred at 0 °C for 5 min followed by dropwise addition of Tf2O (1.5 equiv). The reaction mixture was warmed to room temperature and stirred until full consumption of starting materials (monitored by TLC). The resulting mixture was concentrated under reduced pressure and purified by flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Fluorphenol, Trifluormethansulfonsaeureanhydrid; | ||
3-Fluorphenol-Natrium, Trifluormethansulfonylchlorid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | at 110 - 120℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 76 percent / butyl nitrite / acetic acid 2: 72 percent / 1 h / 110 - 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaOH In tetrachloromethane | ||
With NaOH In tetrachloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
186 mg | With potassium phosphate; chloro(2-dicyclohexylphosphino-2‘,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II); tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one; water; toluene at 90℃; Flow reactor; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With t-BuBrettPhos; water; palladium diacetate; potassium carbonate In <i>tert</i>-butyl alcohol at 110℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With N-Methyldicyclohexylamine; (R)-7-diphenylphosphino-7′-diphenylphosphinyl-1,1′-spirobiindane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 110℃; for 24h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tetra(n-butyl)ammonium hydroxide; palladium diacetate; triphenylphosphine In 1,4-dioxane; water at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With iodine; lithium fluoride; sodium iodide In acetonitrile at 25℃; for 24h; Inert atmosphere; UV-irradiation; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With [COD(Pd-AlPhos)2]; 1,8-diazabicyclo[5.4.0]undec-7-ene In tert-butyl methyl ether at 20℃; for 16h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl-ammonium chloride; sodium formate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; chemoselective reaction; | General Procedure B: General Procedure for Pd nanoparticle reductive-Heck reaction General procedure: To a flame-dried 0.5-dram vial fitted with a rubber septum and equipped with a magnetic stir bar was added aryl triflate (1.0 equiv), Pd2dba3 (10 mol %), TBAC (1.5 equiv) and NaHCO2 (1.2 equiv). The contents were evacuated and backfilled three times with argon. 2,3-Dihydrofuran (DHF) (5.2 equiv) and DMF (0.7 M) was added via syringe and the reaction vial was sealed with a screw-top cap. The reaction mixture was stirred at room temperature for 14-16 hours. The reaction was diluted with Et2O (3 mL) and filtered through a 3 cm pad of silica, flushing with 35 mL of Et2O. The solution was concentrated via rotary evaporation. The reductive-Heck product was isolated by flash chromatography (gradient 2 to 20% EtOAc/hexanes). NOTE: The reaction is sensitive to water. Precaution to exclude moisture from hydroscopic reagents must be taken. DMF was degassed and dried over 3 Å molecular sieves and was stored under argon for up to one week. NaHCO2 was dried in a scintillation vial and lightly heated with a laboratory heat gun under vacuum. It was stored in a dry-box with Drierite (CaSO4) desiccant for up to 1 week. 2,3-Dihydrofuran was purified via short-path distillation under argon. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With tert.-butyl lithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #3: m-fluorophenyl trifluoromethanesulfonate With bis(acetylacetonate)nickel(II); methylmagnesium bromide; triphenylphosphine In tetrahydrofuran at 20℃; for 19h; Inert atmosphere; | 3-Fluoro-3',4'-methylenedioxybiphenyl (Table 2, Entry 14) Procedure 1 According to General Procedure B, Method A, a solution of 4-bromo-1,2-methylenedioxybenzene (402 mg, 2.00 mmol) in THF (10 mL) was sequentially treated with t-BuLi (2.8 mL, 1.58 M, 4.42 mmol) and ZnCl2 (3.0 mL, 1.0 M, 3.00 mmol) and warmed to rt. According to General Procedure D, to a second flask containing Ni(acac)2 (22 mg, 0.084 mmol) and PPh3 (89 mg, 0.34 mmol) in THF (3 mL) was added sequentially solutions MeMgBr (0.10 mL, 3.0 M, 0.30 mmol), the above freshly prepared organozinc solution via canula and a solution of 3-fluorophenyl trifluoromethanesulfonate (188 mg, 1.00 mmol) in THF (2+1 mL). After 19 h reaction, normal workup followed by flash chromatography (4:1 hexane:CH2Cl2) gave the product (161 mg, 74%) as a colourless solid, mp 59-60 °C (pentane); IR (KBr) (max) 2908, 1478, 1233, 1033, 780 cm-1; 1H NMR (200 MHz, CDCl3) 5.96 (s, 2H, OCH2O), 6.84 (d, J = 8.5 Hz, 1H), 6.92-7.03 (m, 3H), 7.15-7.34 (m, 3H); 13C NMR (50 MHz, CDCl3) 101.2 (e, OCH2O), 107.5 (o), 108.6 (o), 113.6 (o, d, J = 21.1Hz), 113.7 (o, d, J = 21.7 Hz), 120.6 (o), 122.4 (o, d, J = 2.6 Hz), 130.1 (o, d, J = 8.9 Hz), 134.2 (e), 143.1 (e, d, J = 7.6 Hz), 147.5 (e), 148.2 (e), 163.1 (e, d, J = 245.6 Hz, CAr-F); MS (EI (60 eV)) m/z (rel intensity) 216 (M+, 100), 157 (13). Anal. Calcd for C13H9FO2: C, 72.22; H, 4.20. Found: C, 72.04; H, 4.42. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol Reflux; | Procedure 4 According to General Procedure E, a solution of 3-fluorophenyl trifluoromethanesulfonate (256 mg, 1.05 mmol) in DME (3 mL) was treated with a solution of 3,4-methylenedioxyphenyl boronic acid (251 mg, 1.51 mmol) in DME (3 mL) and EtOH (3 mL) in the presence of Pd(PPh3)4 (45 mg, 0.039 mmol). After 17 h, the reaction mixture was cooled to rt. Normal workup followed by flash chromatography (9:1 hexane:CH2Cl2) afforded the product (194 mg, 86%) shown to be identical to that prepared in Procedure 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
219 mg | With bis(acetylacetonate)nickel(II); methylmagnesium bromide; triphenylphosphine In tetrahydrofuran; diethyl ether at 20℃; for 24h; Inert atmosphere; | Procedure C. Nickel-catalyzed Coupling of Organozinc Reagents with Organotriflates General procedure: To a stirred solution at rt of nickel catalyst (0.05 mmol) in THF (3 mL) under Ar or N2 was added sequentially either DIBAH or MeMgBr (0.1 mmol), a freshly prepared aryl organozinc solution (2 mmol) via canula and an organotriflate (1 mmol) in THF (2 mL) with an additional amount of THF (1 mL) for quantitative transfer. Once all additions were complete, the reaction mixture was stirred at rt until TLC indicated disappearance of starting material, typically 12-18 h. At this time, the reaction mixture was treated with aq satd NH4Cl and extracted with Et2O. The combined extracts were dried (MgSO4), subjected to filtration, and the filtrate concentrated in vacuo to give a residue which was subjected to flash chromatography on silica gel to afford the diaryl product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetramethylammonium fluoride In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With Trimethyl borate; water; acetone; trifluoroacetic acid at 15℃; UV-irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)nickel (0); acetone; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 140℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With C18H28Cl2N2NiP2; zinc In dimethyl sulfoxide at 100℃; for 48h; Glovebox; Inert atmosphere; Schlenk technique; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With nickel diacetate; zinc; 1,2-bis-(dicyclohexylphosphino)ethane In N,N-dimethyl acetamide at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine; potassium iodide In ethanol at 100 - 200℃; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine; potassium iodide In ethanol at 100 - 200℃; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine; potassium iodide In ethanol at 100 - 200℃; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine; potassium iodide In ethanol at 100 - 200℃; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine; potassium iodide In ethanol at 100 - 200℃; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine; potassium iodide In ethanol at 100 - 200℃; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; triethylamine; potassium iodide In ethanol at 100 - 200℃; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With bis(1,5-cyclooctadiene)nickel (0); C49H49N2(1+)*Cl(1-) In toluene at 40℃; for 5h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With bis(acetonitrile)palladium(II) chloride; tripotassium phosphate tribasic; dicyclohexyl[2’,4’,6’-tris(propan-2-yl)[1,1’-biphenyl]-2-yl]phosphane at 70℃; for 10h; Schlenk technique; Sealed tube; Inert atmosphere; stereoselective reaction; | 3. General Procedure for Synthesis of 2,3-Disubstituted Norbornene. General procedure: An oven-dried 10 mL Schlenk-type tube equipped with a magnetic stir bar was charged with aryl triflate (0.4 mmol), bicyclic alkene (0.72 mmol, 1.8 equiv), terminal alkyne (0.48 mmol, 1.2 equiv), Pd(MeCN)2Cl2 (0.02 mmol, 5 mol%), X-Phos (0.04 mmol, 10 mol%), K3PO4 (0.48 mmol, 1.2 equiv) and PhOMe (1.0 mL). The reaction tube was backfilled with nitrogen three times and well sealed. After the reaction mixture was stirred at 80 °C for 10 h, it was cooled down to ambient temperature. The resulting mixture was diluted with CH2Cl2 (5 mL), dried over Na2SO4, and concentrated in vacuo. Products were obtained by preparative thin-layer chromatography (petroleum ether/ethyl acetate). |
Tags: 57606-65-2 synthesis path| 57606-65-2 SDS| 57606-65-2 COA| 57606-65-2 purity| 57606-65-2 application| 57606-65-2 NMR| 57606-65-2 COA| 57606-65-2 structure
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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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