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[ CAS No. 886371-22-8 ]

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Chemical Structure| 886371-22-8
Chemical Structure| 886371-22-8
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Product Details of [ 886371-22-8 ]

CAS No. :886371-22-8 MDL No. :MFCD02260845
Formula : C8H3Cl2F3O Boiling Point : 225.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :243.01 g/mol Pubchem ID :24726839
Synonyms :

Safety of [ 886371-22-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886371-22-8 ]

  • Upstream synthesis route of [ 886371-22-8 ]
  • Downstream synthetic route of [ 886371-22-8 ]

[ 886371-22-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 106-46-7 ]
  • [ 431-47-0 ]
  • [ 886371-22-8 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at 0℃; for 2.5 h;
Example 1: l-(2,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone A solution of 1 ,4-dichlorobenzene (20 g, 136 mmol) in anhydrous THF (200 mL) was cooled to -78 °C. n-BuLi (150 mmol in 60 mL hexane) was added. The mixture was stirred for 1 h, followed by addition of methyl trifluoroacetate (18 mL, 179 mmol) in 30 min. The mixture was allowed to warm up to 0 °C and then stirred for 2 h. Pre-cooled saturated aqueous ammonium chloride solution (100 mL) was added. The phases were separated. The organic phase was concentrated under vacuum and the residue was dissolved in ethyl acetate (200 mL). The water phase was extracted with ethyl acetate (200 mL). The two ethyl acetate phases were combined and then washed with brine (200 mL). The phases were separated. The organic phase was dried over Na2S04 and then filtrated. The filtrate was concentrated under vacuum. The residue was purified via column chromatography using silica gel eluting with ethyl acetate / hexane (1/10 v/v) to afford after isolation and drying l-(2,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone as an orange oil (28.5 g, 86 percent yield).1H NMR (400 MHz, CDC13) delta 7.67 (s, 1H), 7.56 to 7.50 (m, 2H).
86%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at -78 - 0℃; for 2.5 h;
Example 1: l-(2,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanoneA solution of 1 ,4-dichlorobenzene (20 g, 136 mmol) in anhydrous THF (200 mL) was cooled to -78 °C. n-BuLi (150 mmol in 60 mL hexane) was added. The mixture was stirred for 1 h, followed by addition of methyl trifluoroacetate (18 mL, 179 mmol) in 30 min. The mixture was allowed to warm up to 0 °C and then stirred for 2 h.Pre-cooled saturated aqueous ammonium chloride solution (100 mL) was added. The phases were separated. The organic phase was concentrated under vacuum and the residue was dissolved in ethyl acetate (200 mL). The water phase was extracted with ethyl acetate (200 mL). The two ethyl acetate phases were combined and then washed with brine (200 mL). The phases were separated. The organic phase was dried over Na2S04 and then filtrated. The filtrate was concentrated under vacuum. The residue was purified via column chromatography using silica gel eluting with ethyl acetate / hexane (1/10 v/v) to afford after isolation and dryingl-(2,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone as an orange oil (28.5 g, 86 percent yield).1H NMR (400 MHz, CDC13) delta 7.67 (s, 1H), 7.56 to 7.50 (m, 2H).
86%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at 0℃; for 2.5 h;
Example 1: l-(2,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanoneA solution of 1 ,4-dichlorobenzene (20 g, 136 mmol) in anhydrous THF (200 mL) was cooled to -78 °C. n-BuLi (150 mmol in 60 mL hexane) was added. The mixture was stirred for 1 h, followed by addition of methyl trifluoroacetate (18 mL, 179 mmol) in 30 min. The mixture was allowed to warm up to 0 °C and then stirred for 2 h.Pre-cooled saturated aqueous ammonium chloride solution (100 mL) was added. The phases were separated. The organic phase was concentrated under vacuum and the residue was dissolved in ethyl acetate (200 mL). The water phase was extracted with ethyl acetate (200 mL). The two ethyl acetate phases were combined and then washed with brine (200 mL). The phases were separated. The organic phase was dried over Na2S04 and then filtrated. The filtrate was concentrated under vacuum. The residue was purified via column chromatography using silica gel eluting with ethyl acetate / hexane (1/10 v/v) to afford after isolation and dryingl-(2,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone as an orange oil (28.5 g, 86 percent yield).1H NMR (400 MHz, CDC13) delta 7.67 (s, 1H), 7.56 to 7.50 (m, 2H).
Reference: [1] Patent: WO2012/79235, 2012, A1, . Location in patent: Page/Page column 34
[2] Patent: WO2012/97511, 2012, A1, . Location in patent: Page/Page column 57
[3] Patent: WO2012/97510, 2012, A1, . Location in patent: Page/Page column 56
  • 2
  • [ 106-46-7 ]
  • [ 383-63-1 ]
  • [ 886371-22-8 ]
YieldReaction ConditionsOperation in experiment
77.3%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -75 - -70℃; for 1 h; Cooling with liquid nitrogen
Stage #2: at -80 - -75℃; for 0.5 h;
General procedure: To a chilled to –75 °C solution of 1,4-dichlorobenzene (10.0 g,68 mmol) in anhydrous THF (150 mL), BunLi (30 mL, 75 mmol,2.5 M solution in hexane) was added dropwise maintaining the reaction temperature below –70 °C. The reaction mixture wasstirred at –75 °C for 1 h, cooled to –80 °C with liquid nitrogenand then a solution of ethyl trifluoroacetate (10.8 g, 76 mmol) in THF (15 mL) was slowly added maintaining the reaction temperature below –75 °C. After 30 min stirring at –75 °C, thereaction mixture was warmed up to –50 °C, and 10percent HCl (20 mL) was added following by warming up to 0 °C and additionof another portion of 10percent HCl (10 mL) until distinct acidity ofthe aqueous layer was achieved. The organic layer was separated and the aqueous layer was extracted with diethyl ether (2×40 mL). The combined organics were washed with brine (2×50 mL), dried with Na2SO, and the drying agent was filtered off. The solvents were distilled off under normal pressure using the Vigreux distillation column. Vacuum distillation of the residue afforded 12.8 g (77.3percent) of compound 2b as light yellow liquid. B.p. 92—100 °C (10 Torr), nD20 1.4921.
Reference: [1] Russian Chemical Bulletin, 2014, vol. 63, # 10, p. 2264 - 2270[2] Izv. Akad. Nauk, Ser. Khim., 2014, # 10, p. 2264 - 2270,7
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