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Product Details of [ 1823-63-8 ]

CAS No. :1823-63-8 MDL No. :MFCD09832168
Formula : C8H5F3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IFNQIRKICGIWKF-UHFFFAOYSA-N
M.W : 190.12 Pubchem ID :11446818
Synonyms :

Safety of [ 1823-63-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1823-63-8 ]

* 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.

  • Downstream synthetic route of [ 1823-63-8 ]

[ 1823-63-8 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 711-38-6 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
96% With boron tribromide; In dichloromethane; at -78 - 20℃; for 16h; To a stirred solution of 2,2,2-Trifluoro-l-(4-methoxy-phenyl)-ethanone (8) (500 mg, 2.45 mmol) in DCM (5 mL) was added BBr3 (1M in DCM, 24.4 mL, 24.4 mmol) drop wise at -78C and the reaction mixture was slowly warmed to room temperature and stirred for 16 hours. It was then quenched with aqueous NaHC03 solution and partitioned between Ethyl acetate and water. The organic layer was separated, water, dried over Na2S04 and concentrated under reduced pressure to afford Intermediate 9 (450 mg, 96%) as yellow gum
To a cooled (-780C) solution of 2,2,2-trifluoro-4'-methoxyacetophenone (15 ml, 73 mmol) in DCM was added 1.0 M tribromoborane (73 ml, 73 mmol) drop wise. After the addition was completed, the reaction was slowly warmed to RT and stirred for overnight (15 h). At this point, reaction was completed by TLC. The product mixture was poured into ice water.The organic layer was washed with 10% aq Na2CO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (5-40% EtOAc/hexane) to afford the title compound as a white crystalline solid. The major side product was a colorless oil with MS+ = 379.
  • 2
  • [ 1823-63-8 ]
  • [ 246245-20-5 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate In 1,4-dioxane; isopropyl alcohol at 20℃;
With sodium cyanoborohydride; zinc(II) iodide In 1,1-dichloroethane at 20℃; for 18h; 510.2 To a solution of 2,2,2-trifluoro-l-(4-hydroxyphenyl)ethanone (5.0 g, 26 mmol) in dichloroethane was added zinc iodide (2.7 ml, 39 mmol) followed by sodium cyanoborohydride (10 ml, 197 mmol). The reaction was stirred at RT for 18 h. Both TLC and LCMS showed one product was formed. MS+ = 175 (desired mass 192 - OH). The mixture was filtered through celite and rinsed with dichloromethane. The filtrate was concentrated and dried in vacuum to afford the title compound as colorless oil. MS m/z: 175(M-H2O).
  • 3
  • [ 1823-63-8 ]
  • [ 608880-37-1 ]
  • [ 608880-41-7 ]
YieldReaction ConditionsOperation in experiment
74% With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃;
  • 4
  • [ 1823-63-8 ]
  • poly(ethylene glycol) monomethyl ether, mesylate [ No CAS ]
  • poly(ethylene glycol) methyl 4-(α,α,α-trifluoroacetyl)phenyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 65℃;
  • 5
  • [ 760969-01-5 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
90% With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;
  • 6
  • [ 106-41-2 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / imidazole / dimethylformamide / 0 - 20 °C 2: 56 percent / Mg / tetrahydrofuran / 20 °C 3: 90 percent / TBAF / tetrahydrofuran / 20 °C
  • 7
  • [ 67963-68-2 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 56 percent / Mg / tetrahydrofuran / 20 °C 2: 90 percent / TBAF / tetrahydrofuran / 20 °C
  • 8
  • [ 1823-63-8 ]
  • [ 608880-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C 5: 97 percent / NaOH; MeOH / 20 °C 6: 82 percent / I2; Et3N / methanol / 1 h / 20 °C 7: 80 percent / aq. HCl / tetrahydrofuran / 20 °C
  • 9
  • [ 1823-63-8 ]
  • [ 727975-09-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C 5: 97 percent / NaOH; MeOH / 20 °C 6: 82 percent / I2; Et3N / methanol / 1 h / 20 °C
  • 10
  • [ 1823-63-8 ]
  • [ 608880-45-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C 5: 97 percent / NaOH; MeOH / 20 °C
  • 11
  • [ 1823-63-8 ]
  • [ 608880-44-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C
  • 12
  • [ 1823-63-8 ]
  • [ 608880-42-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C
  • 13
  • [ 1823-63-8 ]
  • [ 608880-43-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C
  • 14
  • [ 354-32-5 ]
  • [ 108-95-2 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
9 EXAMPLE 9 EXAMPLE 9 0.1 mol of phenol and 0.1 mol of trifluoroacetyl chloride are reacted analogously to Example 4 to give 4-trifluoroacetylphenol.
  • 15
  • [ 75-61-6 ]
  • [ 1823-63-8 ]
  • [ 849370-45-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one With sodium hydride In 1,3-dimethyl-2-imidazolidinone at 20℃; for 0.5h; Stage #2: dibromodifluoromethane In 1,3-dimethyl-2-imidazolidinone at 0 - 10℃; Stage #3: With potassium <i>tert</i>-butylate In 1,3-dimethyl-2-imidazolidinone at 20℃; for 1h; 2.1 Step 1; Preparation of 4'-bromodifluoromethoxy-2,2,2-trifluoroacetophenone; To 10 ml of a 1,3-dimethyl-2-imidazolidinone solution containing 2.0 g of 2,2,2-trifluoro-4'-hydroxyacetophenone was added 0.51 g of 55% oily sodium hydride under ice cooling and stirring, and the mixture was stirred at room temperature for 30 minutes. Then, the reaction mixture was added dropwise to 10 ml of a 1,3-dimethyl-2-imidazolidinone solution containing 11.0 g of dibromodifluoromethane under ice cooling and stirring with a rate in which an innter temperature was maintained at 10°C or lower. After completion of the dropwise addition, the temperature of the mixture was raised to room temperature, 0.12 g of potassium t-butoxide was added to the mixture, and then, stirring was continued at the same temperature for further 1 hour. After completion of the reaction, the reaction mixture was poured into 150 ml of ice-water, extracted with 100 ml of diethyl ether, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:19 to 1:9) to obtain 1.83 g of the objective product as yellow oily substance. 1H NMR (CDCl3, Me4Si, 300MHz) δ 8.16 (d, J=8.8Hz, 2H), 7.43 (d, J=8.8Hz, 2H).
  • 16
  • [ 17878-44-3 ]
  • [ 383-63-1 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
68% With n-butyllithium In tetrahydrofuran
  • 17
  • [ 5292-43-3 ]
  • [ 1823-63-8 ]
  • [ 1351283-01-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; potassium iodide In acetonitrile at 120℃; for 0.666667h; Microwave irradiation;
  • 18
  • [ 1823-63-8 ]
  • [ 1351283-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / acetonitrile / 0.67 h / 120 °C / Microwave irradiation 2: pyridine; hydroxylamine hydrochloride / 0.67 h / 70 °C / Microwave irradiation
  • 19
  • [ 1823-63-8 ]
  • [ 1351283-03-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; potassium iodide / acetonitrile / 0.67 h / 120 °C / Microwave irradiation 2: pyridine; hydroxylamine hydrochloride / 0.67 h / 70 °C / Microwave irradiation 3: pyridine / 0.67 h / 140 °C / Microwave irradiation
  • 20
  • [ 1823-63-8 ]
  • [ 1351283-04-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; potassium iodide / acetonitrile / 0.67 h / 120 °C / Microwave irradiation 2: pyridine; hydroxylamine hydrochloride / 0.67 h / 70 °C / Microwave irradiation 3: pyridine / 0.67 h / 140 °C / Microwave irradiation 4: ammonia / -78 °C
  • 21
  • [ 1823-63-8 ]
  • [ 1351283-05-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate; potassium iodide / acetonitrile / 0.67 h / 120 °C / Microwave irradiation 2: pyridine; hydroxylamine hydrochloride / 0.67 h / 70 °C / Microwave irradiation 3: pyridine / 0.67 h / 140 °C / Microwave irradiation 4: ammonia / -78 °C 5: iodine; triethylamine / dichloromethane
  • 22
  • [ 1823-63-8 ]
  • [ 152565-36-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate; potassium iodide / acetonitrile / 0.67 h / 120 °C / Microwave irradiation 2: pyridine; hydroxylamine hydrochloride / 0.67 h / 70 °C / Microwave irradiation 3: pyridine / 0.67 h / 140 °C / Microwave irradiation 4: ammonia / -78 °C 5: iodine; triethylamine / dichloromethane 6: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane
  • 23
  • [ 246245-20-5 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 12h; Reflux;
  • 24
  • [ 123-08-0 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C 1.2: 4 h / Acidic conditions 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 12 h / Reflux
  • 25
  • [ 1823-63-8 ]
  • N-(4-methoxyphenyl)-2,2,2-trifluoro-1-(4-ethylphenoxyacetate)ethan-1-imine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 0 - 60 °C / Inert atmosphere 2: montmorillonite K10 / toluene / 4.5 h / 130 °C / Microwave irradiation
  • 26
  • [ 1823-63-8 ]
  • [ 105-36-2 ]
  • [ 1453102-20-9 ]
YieldReaction ConditionsOperation in experiment
33% With potassium carbonate In N,N-dimethyl-formamide at 0 - 60℃; for 4h; Inert atmosphere;
  • 27
  • [ 1823-63-8 ]
  • C16H24F3(15)NO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: [15N]hydroxylamine hydrochloride; pyridine / ethanol / 3 h / 60 °C / Inert atmosphere; Schlenk technique
  • 28
  • [ 1823-63-8 ]
  • C26H22F6(15)N2O10S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: [15N]hydroxylamine hydrochloride; pyridine / ethanol / 3 h / 60 °C / Inert atmosphere; Schlenk technique 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Schlenk technique 4: triethylamine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Schlenk technique
  • 29
  • [ 1823-63-8 ]
  • C34H32Br2F6(15)N2O12S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: [15N]hydroxylamine hydrochloride; pyridine / ethanol / 3 h / 60 °C / Inert atmosphere; Schlenk technique 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Schlenk technique 4: triethylamine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Schlenk technique 5: triethylamine; dmap / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
  • 30
  • [ 1823-63-8 ]
  • C10H9F3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Schlenk technique
  • 31
  • [ 1823-63-8 ]
  • C14H14BrF3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Schlenk technique 3: triethylamine; dmap / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
  • 32
  • [ 1823-63-8 ]
  • C14H15BrF3NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Schlenk technique 3: triethylamine; dmap / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 4: pyridine; hydroxylamine hydrochloride / ethanol / 4 h / 60 °C / Inert atmosphere; Schlenk technique
  • 33
  • [ 1823-63-8 ]
  • C21H21BrF3NO6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Schlenk technique 3: triethylamine; dmap / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 4: pyridine; hydroxylamine hydrochloride / ethanol / 4 h / 60 °C / Inert atmosphere; Schlenk technique 5: triethylamine / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere
  • 34
  • [ 1823-63-8 ]
  • C14H15BrF3(15)NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere; Schlenk technique 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Schlenk technique 3: triethylamine; dmap / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 4: [15N]hydroxylamine hydrochloride; pyridine / ethanol / 4 h / 60 °C / Inert atmosphere; Schlenk technique
  • 35
  • [ 1823-63-8 ]
  • [ 86864-60-0 ]
  • [ 271252-24-5 ]
YieldReaction ConditionsOperation in experiment
70% With 18-crown-6 ether; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere; Schlenk technique;
  • 36
  • [ 19788-37-5 ]
  • [ 1823-63-8 ]
  • 1-[4-(3,5-dimethylisoxazol-4-ylmethoxy)phenyl]-2,2,2-trifluoroethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; 1 To a stirred solution of ,2,2-Trifluoro-l-(4-hydroxy-phenyl)-ethanone (9) (450 mg, 2.394 mmol) in DMF (5 mL) were added K2C03 (661 mg, 4.787 mmol) and 4-Chloromethyl- 3,5-dimethyl-isoxazole (6) (0.333 mL, 2.633 mmol) and the reaction mixture was stirred at ambient temperature for 16 hours. It was then diluted with Ethyl acetate, washed with water and brine, dried over Na2S04 and concentrated under reduced pressure. Residue was triturated with hexane, decanted and dried well to afford Intermediate 10 (650 mg, 90%) as yellow solid.
  • 37
  • [ 1823-63-8 ]
  • [ 106-93-4 ]
  • C10H8BrF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.8% With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In ethyl acetate Reflux;
  • 38
  • [ 1823-63-8 ]
  • tert-butyl (S)-2-(4-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)phenoxy)propanoate [ No CAS ]
  • tert-butyl (S)-2-(4-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C 4.1: hydroxylamine hydrochloride; pyridine / ethanol / 60 °C
  • 39
  • [ 1823-63-8 ]
  • (S)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux
  • 40
  • [ 1823-63-8 ]
  • (R)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux
  • 41
  • [ 1823-63-8 ]
  • tert-butyl (S)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C
  • 42
  • [ 1823-63-8 ]
  • tert-butyl (R)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C
  • 43
  • [ 1823-63-8 ]
  • tert-butyl (R)-2-(4-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C 4.1: hydroxylamine hydrochloride; pyridine / ethanol / 60 °C
  • 44
  • [ 1823-63-8 ]
  • tert-butyl (R)-2-(4-(2,2,2-trifluoro-1-((tosyloxy)imino)ethyl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C 4.1: hydroxylamine hydrochloride; pyridine / ethanol / 60 °C 5.1: triethylamine; dmap / dichloromethane / 0.75 h / 20 °C
  • 45
  • [ 1823-63-8 ]
  • tert-butyl (R)-2-(4-(3-(trifluoromethyl)diaziridin-3-yl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C 4.1: hydroxylamine hydrochloride; pyridine / ethanol / 60 °C 5.1: triethylamine; dmap / dichloromethane / 0.75 h / 20 °C 6.1: ammonia / diethyl ether / 20 °C / Sealed tube
  • 46
  • [ 1823-63-8 ]
  • tert-butyl (R)-2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C 4.1: hydroxylamine hydrochloride; pyridine / ethanol / 60 °C 5.1: triethylamine; dmap / dichloromethane / 0.75 h / 20 °C 6.1: ammonia / diethyl ether / 20 °C / Sealed tube 7.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C
  • 47
  • [ 1823-63-8 ]
  • (R)-2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 8 h / 0 - 20 °C 2.1: potassium carbonate / methanol; water / 2 h / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 0 - 55 °C 4.1: hydroxylamine hydrochloride; pyridine / ethanol / 60 °C 5.1: triethylamine; dmap / dichloromethane / 0.75 h / 20 °C 6.1: ammonia / diethyl ether / 20 °C / Sealed tube 7.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C 8.1: trifluoroacetic acid / dichloromethane / 20 °C
  • 48
  • [ 17392-83-5 ]
  • [ 1823-63-8 ]
  • methyl (R)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: (R)-Methyl lactate; 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Stage #2: With diethylazodicarboxylate In dichloromethane at 0 - 20℃; for 8h; Methyl (S)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate (S)-33. To 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethanone 31 (1.175 g, 7.25 mmol) in dry CH2Cl2 (30 mL), D-(+)-lactate 4 (1.132 g, 10.9mmol) and PPh3 (2.282 g, 8.70 mmol) was added at 0 °C. After the reaction mixture was stirred for 10min at 0 °C, DEAD (1.891 g, 10.9 mmol) was slowly added at same temperature. The reaction mixturewas stirred overnight at room temperature and partitioned between water and CH2Cl2. The organiclayer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purifiedby column chromatography (ethyl acetate/n-hexane, 1:9) to give (S)-33 (1.560 g, 78%). [α]D -48 (c 1,CHCl3).
  • 49
  • [ 27871-49-4 ]
  • [ 1823-63-8 ]
  • methyl (S)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: (S)-Methyl lactate; 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Stage #2: With diethylazodicarboxylate In dichloromethane at 0 - 20℃; for 8h; Methyl (S)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate (S)-33. To 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethanone 31 (1.175 g, 7.25 mmol) in dry CH2Cl2 (30 mL), D-(+)-lactate 4 (1.132 g, 10.9mmol) and PPh3 (2.282 g, 8.70 mmol) was added at 0 °C. After the reaction mixture was stirred for 10min at 0 °C, DEAD (1.891 g, 10.9 mmol) was slowly added at same temperature. The reaction mixturewas stirred overnight at room temperature and partitioned between water and CH2Cl2. The organiclayer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purifiedby column chromatography (ethyl acetate/n-hexane, 1:9) to give (S)-33 (1.560 g, 78%). [α]D -48 (c 1,CHCl3). 1H-NMR (270 MHz, CDCl3): δ = 7.96 (d, J = 8.2 Hz, 2H), 6.88 (d, J = 8.2 Hz, 2H), 4.82 (q, J = 6.8Hz, 1H), 3.70 (s, 3H), 1.59 (d, J = 6.8 Hz, 3H). 13C-NMR (67.5 MHz, CDCl3): δ = 178.8 (q, 2JCF = 34.6 Hz),171.4, 163.2, 132.7, 123.4, 116.8 (q, 1JCF = 291.4 Hz), 115.2, 72.5, 52.5, 18.3. HRMS (ESI): m/z calculatedfor C12H11F3O4 + H+ [M + H+]: 277.0688. Found: 277.0674.
  • 50
  • C25H20O3P(1+)*Br(1-) [ No CAS ]
  • [ 81290-20-2 ]
  • [ 1823-63-8 ]
YieldReaction ConditionsOperation in experiment
66.5 mg Stage #1: (trifluoromethyl)trimethylsilane With copper(l) iodide; cesium fluoride In acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Sealed tube; Stage #2: C25H20O3P(1+)*Br(1-) In tetrahydrofuran; acetonitrile at 20℃; for 1h; Inert atmosphere; chemoselective reaction;
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