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Chemical Structure| 1069115-04-3 Chemical Structure| 1069115-04-3

Structure of 1069115-04-3

Chemical Structure| 1069115-04-3

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Product Details of [ 1069115-04-3 ]

CAS No. :1069115-04-3
Formula : C10H8BrF3O2
M.W : 297.07
SMILES Code : O=C(OC)CC1=CC=C(C(F)(F)F)C=C1Br
English Name :methyl 2-[2-bromo-4-(trifluoromethyl)phenyl]acetate
MDL No. :MFCD27578361

Safety of [ 1069115-04-3 ]

Application In Synthesis of [ 1069115-04-3 ]

* 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 [ 1069115-04-3 ]

[ 1069115-04-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 474024-36-7 ]
  • [ 1069115-04-3 ]
YieldReaction ConditionsOperation in experiment
92% With sulfuric acid at 0℃; Reflux;
  • 2
  • [ 1069115-04-3 ]
  • [ 1279722-88-1 ]
  • [ 1434044-13-9 ]
YieldReaction ConditionsOperation in experiment
65% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 125℃; for 0.5h; Microwave irradiation; Inert atmosphere; Sealed tube; Condition 2: Synthesis of 5H-dibenzo[b,d]azepin-6(7H)-one (4) General procedure: To a 2-5 mL capacity microwave vial charged methyl 2-(2-bromophenyl)acetate (0.100 g,0.43 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.115 g, 0.523 mmol)and 2 M aqueous sodium carbonate (0.5 mL, 0.86 mmol) in 1,2-dimethoxy ethane (4 mL).The mixture was stirred and degassed with argon for 5 minutes. To this mixture addedPdCl2(PPh3)2 (15 mg, 0.021 mmol) under argon atmosphere, purging continued for another 2minutes. The tube was sealed and irradiated in microwave at 125 °C for 0.5 h. The vial wascooled to ambient temperature in 15 minutes and diluted with ethyl acetate (30 mL) andwashed with water and brine. The organic layer was dried over anhydrous sodium sulfate,filtered and concentrated. The residue obtained was purified by flash columnchromatography by eluting with gradient of 2-20% ethyl acetate in hexane to afford the 5Hdibenzo[b,d]azepin-6(7H)-one (4) as off white solid (0.073 g, 80%).
  • 3
  • [ 1069115-04-3 ]
  • [ 1073371-77-3 ]
  • [ 1434044-10-6 ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: methyl 2-(2-bromo-4-(trifluoromethyl)phenyl)acetate; 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane at 125℃; for 0.5h; Microwave irradiation; Inert atmosphere; Sealed tube; Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 0.166667h; Inert atmosphere; Sealed tube; Condition 1: Synthesis of 5H-dibenzo[b,d]azepin-6(7H)-one (4) General procedure: To a 2-5 mL capacity microwave vial was charged methyl 2-(2-bromophenyl)acetate (0.100g, 0.43 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.115 g, 0.523 mmol)and cesium carbonate (0.280 g, 0.86 mmol) in anhydrous 1,2-dimethoxy ethane (4 mL). Themixture was stirred and degassed with argon for 5 min. To this mixture was added Pd(PPh3)4(25 mg, 0.021 mmol) under argon atmosphere, and purged for 2 min. The tube was sealedand irradiated in microwave at 125 °C for 0.5 h (This is the internal temperature of reactionmixture and monitored on the screen through a sensor). The vial was cooled to 0°C over aperiod of 15 min, followed by addition of 1M potassium tert-butoxide (0.65 mL, 0.65 mmol)solution in THF. The resulting mixture was stirred for 10 minutes and quenched withsaturated ammonium chloride solution. The mixture was diluted with ethyl acetate (30 mL)and washed with water and brine. The organic layer was dried over anhydrous sodiumsulfate, filtered and concentrated. The residue obtained was purified by flash columnchromatography by eluting with gradient of 2-20% ethyl acetate in hexane to afford the 5Hdibenzo[b,d]azepin-6(7H)-one (4) as off white solid (0.075 g, 82%).
 

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