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Chemical Structure| 154598-53-5 Chemical Structure| 154598-53-5

Structure of 154598-53-5

Chemical Structure| 154598-53-5

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Product Details of [ 154598-53-5 ]

CAS No. :154598-53-5
Formula : C8H5ClF3NO
M.W : 223.58
SMILES Code : FC(F)(F)C(C1=CC(Cl)=CC=C1N)=O
MDL No. :MFCD08458216
InChI Key :NOKSRMDODJGCPZ-UHFFFAOYSA-N
Pubchem ID :10987882

Safety of [ 154598-53-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 154598-53-5 ]

* 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 [ 154598-53-5 ]

[ 154598-53-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 383-63-1 ]
  • [ 65854-91-3 ]
  • [ 154598-53-5 ]
YieldReaction ConditionsOperation in experiment
57 g (54%) In tetrahydrofuran; hydrogenchloride; n-butyllithium; hexane; ethyl acetate; Step B: 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone To an oven dried, 3L, 3 necked round bottomed flask with an overhead stirrer, argon inlet, and a 500 mL oven dried addition funnel was added <strong>[65854-91-3]N-(4-chlorophenyl)-2,2-dimethylpropanamide</strong> (100 g, 472 mmol) and dry THF (1L). This solution was cooled in an ice bath to 0 C. and the addition funnel was charged with n-butyllithium (387 mL of a 2.5 M solution in hexanes, 968 mmol). The n-butyllithium solution was added dropwise to the amide solution slowly over 1 h, maintaining the temperature below +5 C. The resulting solution was aged at 0 C. for 1 h during which time an orange precipitate formed. To this mixture was added ethyl 1,1,1-trifluoroacetate (115 mL, 968 mmol), dropwise over 1 h. The resulting clear solution was aged an additional 30 min. The reaction was quenched with 5% aqueous HCl. The mixture was diluted with 1L of EtOAc and the layers were separated. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo, to give 160 g of a yellow oil. This material was suspended in 1L of 3N aqueous HCl and the solution was heated at reflux for 24 h. The cooled solution was diluted with 1L of EtOAc and the mixture was made basic with concentrated NH4 OH. The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered, concentrated in vacuo, and chromatographed on 1.5 kg of silica gel using 15 % EtOAc in hexane as eluant. The chromatographed material was recrystallized from boiling hexane to give 57 g (54%) of pure 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone as bright yellow crystals, mp: 91-92 C. 1H NMR (CDCl3): delta6.46 (br s, 2H), 6.69 (d, 1H, J=9.2 Hz), 7.32 (dd, 1H, J=2.4, 9.2 Hz), 7.70 (d, 1H, J=2.4 Hz).
  • 3
  • [ 173676-59-0 ]
  • [ 154598-53-5 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydrogencarbonate; In water; at 20℃; for 0.05h;Inert atmosphere; Schlenk technique; A hydrochloride-hydrate adduct of 2g (407 mg, 1.46 mmol) was placed in a 15-mL screw-capvial. To this, a saturated NaHCO3 aqueous solution (2.0 mL) was added, and the resulting mixturewas stirred at room temperature for 3 min. The aqueous phase was extracted with EtOAc (5 mL × 3).The combined organic layer was washed with brine (2 mL) and then dried over anhydrous sodiumsulfate (Na2SO4). Filtration and evaporation of the solvent left a residue, which was successivelypassed through a pad of silica gel using EtOAc to give analytically pure 2g in 99% yield (324 mg) as ayellow solid (m.p. 92-94 C). Compound 2g has already appeared in the literature [87], and itsspectral and analytical data are in good agreement with those reported. Accordingly, only the1H-NMR data are provided here. 1H-NMR (400 MHz, CDCl3) delta 6.47 (bs, 2H), 6.70 (d, J = 8.9 Hz, 1H),7.33 (dd, J = 9.0, 2.4 Hz, 1H), 7.66-7.75 (m, 1H).
With sodium carbonate; In dimethoxyethane (DME);pH 9; 1 -f2-Amino-5-chlorophenyl)-2,2,2-1rifluoroethanone (8-3)6N Hydrochloric acid (6.0M, 257 mmol) was added to N-[4-chloro-2-(trifluoroacetyl)phenyl]-2,2-dimethylpropanamide (3.3 g, 10.7 mmol) in anhydrous dimethoxyethane (40 ml) at room temperature and mixture was heated to reflux conditions for two hours until no starting material was observed by LC/MS. After cooling reaction to 00C, reaction was basified to pH 9 by adding solid sodium bicarbonate in portions. Reaction was extracted with ethyl acetate (3x150ml), and EPO <DP n="38"/>combined organic extracts were dried over MgSO4 and Na2SO4. After filtering mixture, the collected filtrate was concentrated in vacuo to give a crude yellow solid. Flash chromatography of the crude solid on silica gel (0-25% ethyl acetate/hexanes) afforded l-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta 7.70 (m, IH), 7.32 (dd, J=2.4 and 9.2 Hz, IH), 6.68 (d, J= 8.8 Hz, IH), 6.46 (s, 2H). MS (Electrospray): m/z 223.9 (M+).
With sodium hydrogencarbonate; In water; toluene; at 20℃;pH 7 - 8; Example 1; Preparation of 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone (2): A solution of <strong>[173676-59-0]1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone hydrochloride</strong> hydrate (48.5 g, 174.4 mmol), 300 mL toluene, and 150 mL water was stirred at room temperature for 30 minutes. The pH of the solution was adjusted to 7-8 via the addition of saturated aqueous NaHCO3 solution. The resulting mixture was then separated, and the toluene layer was collected and evaporated to dryness to give 38.2 g 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone (2) as a yellow solid.
 

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Technical Information

• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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