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Chemical Structure| 29835-28-7 Chemical Structure| 29835-28-7

Structure of 29835-28-7

Chemical Structure| 29835-28-7

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Product Details of [ 29835-28-7 ]

CAS No. :29835-28-7
Formula : C9H5BrO2
M.W : 225.04
SMILES Code : O=C(O)C#CC1=CC=CC(Br)=C1
MDL No. :MFCD15147227
Boiling Point : No data available
InChI Key :SATQURHUBJUFTF-UHFFFAOYSA-N
Pubchem ID :12330266

Safety of [ 29835-28-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 29835-28-7 ]

* 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 [ 29835-28-7 ]

[ 29835-28-7 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 29835-28-7 ]
  • [ 53060-04-1 ]
  • 4
  • 3-bromo-<i>trans</i>-cinnamic acid ethyl ester [ No CAS ]
  • [ 29835-28-7 ]
  • 5
  • [ 591-18-4 ]
  • [ 471-25-0 ]
  • [ 29835-28-7 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 5h;Inert atmosphere; General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 5h;Inert atmosphere; General procedure: Compounds (1b-1o) were prepared according to literature.17 To a mixture of Pd(PPh3)2Cl2 (70 mg, 2 mol%), CuI (38 mg, 4 mol%) and DMF (7 mL) taken in a flask, aryl iodide (5.0 mmol), propiolic acid (414 mg, 6.0 mmol) and diisopropylamine (1.30 g, 12.5 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through Celite bed, the filtrate was washed with cold aqueous KOH solution (1 x 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuum at 40 C, dried to get the arylpropiolic acids.
  • 6
  • [ 29835-28-7 ]
  • [ 143321-89-5 ]
  • [ 93716-78-0 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate; L-proline; copper(I) bromide; In dimethyl sulfoxide; at 100℃; for 3h;Inert atmosphere; General procedure: To a mixture of Pd(PPh3)2Cl2 (2 mol %), CuI (4 mol %) and DMF (15 mL) taken in a flask, aryl iodide (10 mmol), propiolic acid (12 mmol) and diisopropylamine (25 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through celite bed, the filtrate was washed with cold aqueous KOH solution (1 × 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuo at 40 C, dried to get the arylpropiolic acid. Arylpropiolic acid (5 mmol) or 2-butynoic acid (5 mmol) was transferred into a 30 mL glass tube and then iodo compound (5 mmol), l-proline (15 mol %), cuprous bromide (5 mol %) and potassium carbonate (10 mmol) in DMSO or DMF (10 mL) were added in that order. The sealed tube was then subjected to a vacuum and refilled with nitrogen for five times under stirring at room temperature. The tube was placed in an oil bath and heated with stirring at 100 C for 3-5 h. After the reaction, the reaction mixture was mixed with ethyl acetate and washed with water, brine solution and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo and purification of the residue by silica-gel column chromatography with hexane/ethyl acetate afforded the desired product. See Supplementary data for spectral data of all compounds.
  • 7
  • [ 124-38-9 ]
  • [ 766-81-4 ]
  • [ 29835-28-7 ]
YieldReaction ConditionsOperation in experiment
97% With C76H124N6Nd2O6Si4; caesium carbonate; In dimethyl sulfoxide; at 40℃; under 760.051 Torr; for 24h;Inert atmosphere; Under anhydrous anaerobic, argon protection, 0.0600 g (3.71 x 10-5 mol) of {LNd [N (SiMe3) 2] · THF} 2 was added to the reaction flask. Then 0.6033 g (1.85 x 10-3 moles) of cesium carbonate was added, under the protection of carbon dioxide bags, 2 ml of dimethyl sulfoxide was added. 0.112 ml (9.28 x 10-4 mol) of 3-bromophenylacetylene was added. Then 3 ml of dimethyl sulfoxide was added. The reaction was stirred in a constant temperature bath at 40 C. After 24 hours, 10 mL of water was added to the quench the reaction, and then filtered. The clear solution was placed in a separatory funnel, a certain amount of hydrochloric acid solution was added to acidify, extracted four times with ether, the extract was washed twice with saturated brine, separated, solvent was spin-dried, and then the residual solvent was removed by pumping to obtain the product. The calculated yield was 97%.
90% With caesium carbonate; In dimethyl sulfoxide; at 60℃; under 760.051 Torr; for 24h; Add 4 ml of dimethyl sulfoxide, 1 mmol of 3-bromophenylacetylene, and 2 mmol of cesium carbonate into the reaction tube,The reaction tube was pumped and ventilated 3 times, and filled with CO2. After the CO2 was filled, the gas pressure of the reaction tube was 1 atm. The reaction tube was stirred for 24 hours under the conditions of carbon dioxide atmosphere and 60C. The stirring rate is 800 rpm, stop stirring, and cool to room temperature.Add water to the reaction liquid, extract 4 times with ethyl acetate, separate the layers, take the water layer, acidify the water layer with 2 moles of hydrochloric acid per liter to pH=1, then extract with ethyl acetate, take the organic layer, and wash the organic layer with saturated brine It was dried over magnesium sulfate, the filtrate was filtered, and concentrated under reduced pressure to obtain the target product with a yield of 90%.
78% With sodium acetate; tetraoctyl ammonium bromide; copper(I) bromide; In acetonitrile; at 25℃; under 11251.1 Torr; for 16h;Inert atmosphere; Cuprous bromide (28 mg, 0.2 mmol), sodium acetate (272 mg, 2 mmol), tetra-n-octylammonium bromide (1093.6 mg, 2 mmol), m -bromophenylacetic acid (181 mg, ), Followed by addition to a 25mL reactor, evacuated nitrogen three times, under nitrogen was added refined acetonitrile (4.0mL), charged with CO2 (1.5MPa). The reaction kettle was closed and placed in a 25 C oil bath for 16 h. After the reaction was over, the valve on the kettle was slowly opened to release the remaining gas. The reaction mixture in the autoclave was transferred to a single-neck flask for concentration and diluted with 5 mL of deionized water , And then extracted with n-hexane. The aqueous layer was acidified to pH = 1 at low temperature by addition of 1 M hydrochloric acid and extracted with ether. The organic phase was collected, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo to afford M - Bromophenolic acid, yield 78%.
  • 9
  • [ 29835-28-7 ]
  • [ 98-80-6 ]
  • [ 40396-54-1 ]
  • 10
  • [ 29835-28-7 ]
  • [ 73183-34-3 ]
  • (E)-2-(2-(3-bromophenyl)vinyl-1,2-D<SUB>2</SUB>)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • 11
  • [ 288-13-1 ]
  • [ 29835-28-7 ]
  • C12H7BrN2O [ No CAS ]
  • 13
  • [ 29835-28-7 ]
  • [ 73183-34-3 ]
  • [ 1253943-66-6 ]
YieldReaction ConditionsOperation in experiment
83% With copper(II) trifluoroacetate; sodium carbonate; In 1,4-dioxane; at 80℃; for 18h;Inert atmosphere; General procedure: A Schlenk tube with a magnetic stirring bar was charged with 3-phenylpropiolic acid (1a, 68 mg, 0.5 mmol), bis(pinacolato)diboron (2a, 152 mg, 0.6 mmol), Cu(TFA)2 (29 mg, 10 mol%), Na2CO3 (127 mg, 1.2 mmol), and 1,4-dioxane (2 mL) under N2. The reaction mixture was stirred at 80 C for 18 h (monitored by TLC and GC). Upon completion of the reaction, the reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate (20 mL), filtered through a plug of silica gel, and washed with ethyl acetate (20 mL). The organic layer was washed with saturated brine (20 mL×2) and dried over anhydrous Na2SO4. The solvents were removed via rotary evaporator and the residue was purified by flash chromatography (silica gel, ethyl acetate: petroleum ether=1:30) to give 89.7 mg of desired product 3a in 78 % yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.48-7.50 (m, 2H), 7.41 (d, 1H, J=18.5Hz), 7.29-7.32 (m, 3H), 6.18 (d, 1H, J=18.4Hz), 1.32 (s, 12H). 13C NMR (100 MHz, CDCl3): δ 148.5, 136.4, 127.9, 127.5, 126.0, 82.3, 23.8
  • 14
  • [ 29835-28-7 ]
  • [ 81290-20-2 ]
  • [ 7119-08-6 ]
YieldReaction ConditionsOperation in experiment
53% General procedure: A mixture of CuI (76 mg, 0.4 mmol), phen (79 mg, 0.4 mmol), Ag2CO3 (220 mg, 0.8 mmol), KF (69 mg, 1.2 mmol) and DMF (6 mL) was added to a 25 mL round-bottom flask that was equipped with a magnetic stir bar at room temperature in a glove box. The round bottom flask was sealed with a rubber plug and taken out. Then the flask was evacuated and refilled with nitrogen for three times. Next, Me3SiCF3 (294 mL, 2.0 mmol) was added to the mixture dropwise in 5 min and the mixture was stirred at room temperature for 30 min. A solution of arylpropiolic acids (0.4 mmol) in 1.0 mL DMF was added to the flask during 4 h by using a syringe pump at room temperature. After the addition, the reaction mixture was kept for another 2 h at room temperature. At the end of reaction, dichloromethane (DCM) was added to the reaction system. The organic layer was separated and washed with water three times. The combined organic extracts was dried over Na2SO4 for 2 h and then concentrated under vacuum. After evaporation, the residue was purified by silica gel column chromatography with petroleum ether to provide pure desired products.
  • 15
  • [ 56183-69-8 ]
  • [ 29835-28-7 ]
  • [ 1345719-56-3 ]
YieldReaction ConditionsOperation in experiment
30% With pyridine; copper(II) sulfate; In N,N-dimethyl-formamide; at 70℃; for 12h; General procedure: Diaryl hydrazinylphosphonate (1.2 mmol), arylpropiolic acids (0.3 mmol) and CuSO4 (30 mol%) were dissolved in DMF (1 mL) and stirredat 70 C for 12 h under dry air. The resulting mixture was concentrated under vacuum and the crude product was purified by silica gel chromatography using a mixture of petroleum ether and ethyl acetate as eluent.
  • 16
  • [ 7648-30-8 ]
  • [ 29835-28-7 ]
  • ethyl 4-(3-bromophenyl)-2,2-difluoro-4-iodobut-3-enoate [ No CAS ]
  • C12H10BrF2IO2 [ No CAS ]
  • 17
  • [ 29835-28-7 ]
  • [ 1273583-83-7 ]
  • 18
  • [ 29835-28-7 ]
  • [ 513-42-8 ]
  • 2-methylprop-2-en-1-yl 3-(3-bromophenyl)prop-2-ynoate [ No CAS ]
  • 19
  • [ 29835-28-7 ]
  • 2,2,2-tribromo-1-(3-bromophenyl)ethanone [ No CAS ]
  • 20
  • [ 29835-28-7 ]
  • 1-bromo-3-(1,2,2-tribromovinyl)benzene [ No CAS ]
  • 21
  • [ 29835-28-7 ]
  • [ 1950-68-1 ]
  • 1-(4-methoxyphenyl)-2-(3-bromophenyl)acetylene [ No CAS ]
  • 22
  • [ 3132-99-8 ]
  • [ 29835-28-7 ]
  • 23
  • [ 124-38-9 ]
  • 1-bromo-3-(2',2'-dibromovinyl)benzene [ No CAS ]
  • [ 29835-28-7 ]
  • 24
  • [ 29835-28-7 ]
  • 1-bromo-3-(1-fluoro-2,2-diiodovinyl)benzene [ No CAS ]
  • 25
  • [ 29835-28-7 ]
  • [ 115-19-5 ]
  • 5-(3-bromophenyl)-2-methyl-3-methylenepent-4-yn-2-ol [ No CAS ]
  • 26
  • [ 29835-28-7 ]
  • (Z)-1-benzyl-3-(3-bromobenzylidene)-4-(prop-1-en-2-yl)pyrrolidine-2,5-dione [ No CAS ]
  • 27
  • [ 29835-28-7 ]
  • C21H18BrNO2 [ No CAS ]
  • 28
  • [ 29835-28-7 ]
  • [ 100-46-9 ]
  • C16H12BrNO [ No CAS ]
  • 29
  • [ 29835-28-7 ]
  • [ 842155-19-5 ]
  • 2-(3-bromophenyl)-2-oxoethyl 3-(3-bromophenyl)-propiolate [ No CAS ]
  • 30
  • [ 29835-28-7 ]
  • [ 536-74-3 ]
  • 2-(3-bromophenyl)-2-oxoethyl 3-(3-bromophenyl)-propiolate [ No CAS ]
  • 2-oxo-2-phenylethyl 3-(3-bromophenyl)propiolate [ No CAS ]
  • 31
  • [ 13146-23-1 ]
  • [ 29835-28-7 ]
  • 2-(3-bromophenyl)-2-oxoethyl 3-(3-bromophenyl)-propiolate [ No CAS ]
  • 2-oxo-2-phenylethyl 3-(3-bromophenyl)propiolate [ No CAS ]
  • 32
  • [ 7677-24-9 ]
  • [ 29835-28-7 ]
  • (E)-3-(3-bromophenyl)-2-cyanoacrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With diphenyl(methyl)phosphine; In toluene; at 20℃; for 16h;Schlenk technique; Inert atmosphere; General procedure: (E)-2-cyano-3-phenylacrylic acid (2r). 3-phenylpropiolic acid 1r (2.5 mmol, 1 eq) and toluene (2.5 mL) were mixed together under atmosphere of nitrogen, in test tube previously dried under vacuum. While gentle stirring, TMSCN was added (3 mmol, 1.2 eq), which was followed by dissolution of the acid (DANGER: hydrogen cyanide is formed in this reaction and the reaction must be conducted in the fume hood with proper ventilation). After acid was dissolved and PPh2Me (10 mol %) was added, reaction mixture was stirred at room temperature for 16 hours. Reaction was quenched with water (3 mmol, 1.2 eq) and venously stirred for 10 minutes. Formed precipitate was filtered under vacuum, washed with cold toluene and dried under vacuum to give clean product 2r in form of white crystals, without further purification (307 mg, 71 %)
 

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