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[ CAS No. 175543-23-4 ] {[proInfo.proName]}

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Chemical Structure| 175543-23-4
Chemical Structure| 175543-23-4
Structure of 175543-23-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 175543-23-4 ]

CAS No. :175543-23-4 MDL No. :MFCD12404934
Formula : C10H9F3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QTJOXVLRFWKBMD-UHFFFAOYSA-N
M.W : 218.17 Pubchem ID :11020343
Synonyms :

Safety of [ 175543-23-4 ]

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

Application In Synthesis of [ 175543-23-4 ]

* 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 [ 175543-23-4 ]

[ 175543-23-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1813-94-1 ]
  • [ 175543-23-4 ]
YieldReaction ConditionsOperation in experiment
75.5% With diethylamino-sulfur trifluoride at 60℃; for 4h;
  • 2
  • [ 462-06-6 ]
  • [ 698378-63-1 ]
  • [ 175543-23-4 ]
  • ethyl α,α-difluoro-α-(o-fluorophenyl)acetate [ No CAS ]
  • [ 698378-81-3 ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 8h; Irradiation;
  • 3
  • [ 352-34-1 ]
  • [ 667-27-6 ]
  • [ 175543-23-4 ]
YieldReaction ConditionsOperation in experiment
74% With copper In dimethyl sulfoxide at 55℃; for 12h; Inert atmosphere;
55% With copper In dimethyl sulfoxide at 90℃; 1.175.1 Step 1. ethyl 2,2-difluoro-2-(4-fluorophenyl)acetate A mixture of i-tiuoro-4-iodubenzene (15.0 g, 67.6 rnmob, ethyl 2-bromo-2,2- difluoroacetate (14.5 g, 71 mmol) and copper powder (10,8 g, 35.6 mmol) in DM80 (50 mE) was heated to 90 °C. After stirring overnight at 90 t. the mixture was cooled down to it, and diluted with EtOAc. A solution of K211P04.3H20 (10 g) in water (100 niL) was added into the above mentioned mixture. ‘I’he mixture was stirred for 30 mm and filtered through a pad of celite. The filler mass was extracted with Et0Ac. The combined organic phases were washed with water and brine, drted over Na2S()4 and concentrated. The concentrate was purified, by column chromatography over silica gel (eluent: 100% hexane) to afford the title compound as a colorless oil (8.1 g, 55%). MS (ESI) calcd for CH)F,02 ‘‘218.20: found:[M±Hj. 111 NMR (400 MHz, CIXI) 8 7.61 (dd, ,J 8.4, 5.2 Hz, 211), 7.14 (1, J 8.6 Hz. 211), 4.30 (q,,j:::: T6 Hz, 211), 1.31 (t, J:::: 7.6 liz, 3W),
Stage #1: 4-fluoro-1-iodobenzene; Ethyl bromodifluoroacetate With copper In N,N-dimethyl-formamide at 90℃; for 18h; Stage #2: With potassium dihydrogenphosphate In water; ethyl acetate; N,N-dimethyl-formamide for 0.5h; 11.1 Example 11; Synthesis ofiV-(l-cyanocyclopropyl)-3-cyclopropylmethanesulfonyl-2(i?)-[2,2-difluoro-2-(4- fluorophenyl)- 1 (ιS)-(4-fluorophenyl)ethylamino]propionamide Step 1 l-Fluoro-4-iodobenzene (3O g, 135 mmol) and 2-bromo2,2-difluoroacetic acid ethyl ester (29 g, 142.9 mmol) were dissolved in DMF (100 ml) and Cu (21.5 g, 71.2 mmol) was added. The reaction mixture was heated at 90 0C for 18 h. Ethyl acetate (100 ml) was added and the reaction mixture was quenched with a solution of potassium dihydrogen phosphate (20 g) in water (200 ml). The resultant solution was stirred for 30 min, filtered and was washed with ethyl acetate. The EPO organic layer was separated, washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to give 2,2-difluoro-2-(4-fluorophenyl)acetic acid ethyl ester (26.5 g) as a yellow liquid.
With copper In dimethyl sulfoxide at 60℃; for 12h; Inert atmosphere;
With copper In dimethyl sulfoxide at 60℃; for 12h; Inert atmosphere;
With copper In dimethyl sulfoxide at 60℃; for 12h; Inert atmosphere; 1.2 Preparation of N-(2,2-difluoro-2-phenylethyl) picolinamide General procedure: General Procedure A: In a 50 mL round bottom flask under an atmosphere of N2, the appropriate aryl iodide (10 mmol, 1.0 equiv) and ethyl bromodifluoroacetate (1.3 mL, 10 mmol, 1.0 equiv) were added to a suspension of activated Cu powder (1.7 g, 26 mmol, 2.6 equiv) in DMSO (26 mL, 0.4 M). The reaction mixture was stirred at 60 °C for 12 h, after which time it was poured into a mixture of ice and sat. aq. NH4Cl, the aqueous phase was extracted with EA (3 × 50 mL). The combined organic phases were washed with sat. aq. NH4Cl (2 × 50 mL) and brine (2 × 50 mL), then dried over MgSO4, filtered, and concentrated in vacuo. The crude mixture was purified by flash column chromatography. A solution of the above ethyl α, α-difluoroaryl acetate and NH3 in MeOH (7 M, 10 mL) were stirred at room temperature for 2 h and concentrated to afford α, α-difluoroaryl acetamide. To a s solution of α, α-difluoroaryl acetamide (4 mmol, 1.0equiv) in THF (5 mL) was added borane in THF (1 M, 20 mL, 20 mmol, 5.0 equiv) at 0 °C. After refluxed 70°C for 12 h, then cooled to 0 °C. The reaction mixture was quenched by 4 M HCl in MeOH, after refluxed at 70 °C for 2 h, concentrated to afford α, α-difluoroaryl ethylamine. A mixture of α, α-difluoroaryl ethylamine (6 mmol, 1.0 equiv), picolinic acid (11mmol, 1.1 equiv), HATU (2.1 g, 11 mmol, 1.1 equiv), Et3N (5.2 mL, 30 mmol, 4.0 equiv) in anhydrous CH2Cl2 (20 mL) were stirred at room temperature overnight. Water was added and the mixture was extracted with CH2Cl2. The combined organic layer was washed with water and brine, dried over anhydrous Mg2SO4, and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography to give the desired picolinamide product. Compound 1a-1o was isolated (Rf =0.30, 20% EtOAc in hexanes)

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