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[ CAS No. 28179-33-1 ] {[proInfo.proName]}

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Chemical Structure| 28179-33-1
Chemical Structure| 28179-33-1
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Product Details of [ 28179-33-1 ]

CAS No. :28179-33-1 MDL No. :MFCD01419855
Formula : C14H11BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 291.14 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 28179-33-1 ]

* 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 [ 28179-33-1 ]

[ 28179-33-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 5031-78-7 ]
  • [ 28179-33-1 ]
YieldReaction ConditionsOperation in experiment
69% With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 20℃; for 22h;Reflux; Step 1 [0123] Phenyltrimethylammonium tribromide (1.8 g, 4.7 mmol) was added to a solution of 4'-phenoxyacetophenone (XIII-1) (1.0 g, 4.7 mmol) in tetrahydrofuran (5 mL), and the resultant mixture was stirred for 14 hours at room temperature, then heated under reflux for 8 hours. After leaving to cool, the reaction solution was diluted with water, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate. The solvent was removed under reduced pressure, and then the resultant product was purified by column chromatography (silica gel) to obtain compound (II-9) (amount 1.0 g, yield 69%).
69% With phenyltrimethylammonium tribromide; In tetrahydrofuran; for 8h;Reflux; Step 1 Phenyltrimethylammonium tribromide (1.8 g, 4.7 mmol) was added to a solution of 4'-phenoxyacetophenone (XIII-1) (1.0 g, 4.7 mmol) in tetrahydrofuran (5 mL), and the resultant mixture was stirred for 14 hours at room temperature, then heated under reflux for 8 hours. After leaving to cool, the reaction solution was diluted with water, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate. The solvent was removed under reduced pressure, and then the resultant product was purified by column chromatography (silica gel) to obtain compound (II-9) (amount 1.0 g, yield 69%).
44% With toluene-4-sulfonic acid; In ethyl acetate; at 80℃; for 6h; [00303] A solution of l-(4-phenoxyphenyl) ethan-l-one (2.0 g, 9.0 mmol), CuBn (2.1 g, 9.1 mmol) and TsOH (162 mg, 0.9 mmol) in EA (20 mL) was stirred at 80 C for l6h. T mixture was cooled to rt and filtered. The precipitate was washed with EA (200 mL). The filtrate was concentrated and. the crude product was purified by silica gel chromatography (PE/EA=200/l) to give compound 3.1 as a yellow solid (1.2 g, Y: 44%). ESI-MS (M+H) +: 291.1. NMR: (400 MHz, DMSO-e) d: 8.03 (d, J=8.8, 2H), 7.47 (t, =7.6, 2H), 7.28-7.25 (m, 1H), 7.15 (d, =7.6, 2H), 7.15 (d, =8.8, 2H), 4.87 (s, 2H).
With bromine; In chloroform; acetic acid; at 20℃; for 1h;Inert atmosphere; To a solution of 4 (500 mg, 2.36 mmol) in CHCl3 (5.9 mL) and AcOH (5.9 mL) was added Br2 (377 mg, 2.36 mmol) in CHCl3 (0.5 mL). The mixture was stirred at room temperature for 1 h and the solvent was evaporated under reduced pressure. According to a literature procedure, the residue was dissolved in MeCN (11.8 mL), and 2-hydroxy-5-methoxybenzaldehyde (359 mg, 2.36 mmol) and K2CO3 (978 mg, 7.08 mmol) were added. The mixture was stirred at 70 C for 5 h and cooled. The mixture was diluted with EtOAc and washed with water and brine. The organic fraction was dried over MgSO4 and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (EtOAc-hexane) and crystallized from EtOAc to provide compound 5 (592 mg, 73%) as a white solid.
With copper(ll) bromide; In chloroform; ethyl acetate; for 2h;Reflux; General procedure: Copper(II) bromide (0.050mol) and acetophenone (0.025mol) to be brominated (0.03mol) were placed in a flak fitted with a reflux condenser. Ethyl acetate (25mL) and chloroform (25mL) were added. The resulting reaction mixture was refluxed with vigorous stirring to ensure complete exposure of the copper(II) bromide to the reaction medium until the reaction was complete as judged by a color change of the solution from green to amber, disappearance of all black solid, and cessation of hydrogen bromide evolution. The copper(I) bromide was collected by filtration and washed well with ethyl acetate. The solvents were removed from the filtrate under reduced pressure. The resulting product, 2-bromoacetophenone, was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (25:1) as the mobile phase. A solution of 2-bromoacetophenone (0.0628mol) and hexamethylenetetramine (9.67g, 0.07mmol) in CHCl3 (50mL) was stirred at room temperature for 2h. The precipitated solid was filtered and washed with CHCl3 to obtain quaternary ammonium compounds, which was used in the next step without further purification. Concentrated HCl (30mL) was dropped into the solution of quaternary ammonium in ethanol (100mL). The reaction mixture was stirred at room temperature for 48h. The white solid was removed by filtration and the filtrate was concentrated in vacuo. Recrystallization of the crude product yielded the desired product 2-aminoacetophenone as a white needle-like crystal. To a DMF (10mL) solution of aldehydes (2mmol) were successively added 2-aminoacetophenone hydrochloride (4mmol), iodine (0.6mmol), TBHP (300muL), NaHCO3 (2mmol). After the reaction mixture was stirred for 10h at 70C, the reaction mixture was extracted with EtOAc, washed with diluted HCl followed by water, dried with Na2SO4. Then solvent was removed under reduced pressure and purified by silica gel column chromatography (CH2Cl2/MeOH=40:1) to afford the desired product.
With copper(ll) bromide; In chloroform; ethyl acetate; for 2h;Reflux; The 1 (4-phenoxy-phenyl) - ethanone 0.5mol added a mixed solution of chloroform and 150mL of ethyl acetate was added with stirring 22.3g CuBr2.The reaction was refluxed for 2 hours, filtered hot and washed with chloroform.The mixed solution was washed with water, dried, and evaporated to dryness to give a brown solid, 2-bromo-1- (4-phenoxy-phenyl) - ethanone.The resulting 2-bromo-1- (4-phenoxy-phenyl) - ethanone was added 50mL of chloroform, after complete dissolution, stirring was added 9.67g hexamethylene tetramine.The reaction temperature for 4 hours, cooled to 0 deg.] C, for 2 hours.Filtration, the solid was added 100mL of ethanol, 30mL of concentrated hydrochloric acid was added dropwise, the reaction temperature for 48 hours.Filtered and the solution evaporated to dryness, recrystallized from ethanol, to give 2-amino-1- (4-phenoxy-phenyl) - ethanone hydrochloride
With copper(ll) bromide; In chloroform; ethyl acetate;Reflux; General procedure: Copper (II) bromide (0.050mol) andacetophenoneto be brominated (0.03mol) were placed ina flakfitted with a reflux condenser. Ethyl acetate (25 mL) and chloroform (25 mL) were added. The resulting reaction mixture was refluxed with vigorous stirring to ensure complete exposure of the copper (II) bromide to the reaction medium until the reaction was complete as judged by a color change of the solution from green to amber, disappearance of all black solid, and cessation of hydrogen bromide evolution. The copper (I) bromide was collected by filtration and washed well with ethyl acetate. The solvents were removed from the filtrate under reduced pressure. The resulting product, 2-Bromoacetophenone, was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (25:1) as the mobile phase.

  • 2
  • [ 5031-78-7 ]
  • [ 28179-33-1 ]
  • [ 54916-27-7 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; bromine
With bromine; acetic acid
  • 4
  • [ 6972-05-0 ]
  • [ 28179-33-1 ]
  • [ 1262983-56-1 ]
YieldReaction ConditionsOperation in experiment
89% With tert-butylammonium hexafluorophosphate(V) In methanol at 20℃; for 0.216667h;
  • 5
  • [ 60827-45-4 ]
  • [ 28179-33-1 ]
  • [ 1207291-26-6 ]
  • [ 1207291-25-5 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; at 130℃;Product distribution / selectivity; Example 23; Synthesis of (4S)-trans-,cis-2-(4-chlorophenyl)-2-bromomethyl-4-chloromethyl-1,3-dioxolane suppressing halogen exchange between substrates A mixture of 2-bromo-4'-chloroacetophenone (4.94 g, 2-chloro-4'-chloroacetophenone content=0.09%), p-toluenesulfonic acid monohydrate (0.20 g, 0.05 equivalent) and toluene (100 mL) was refluxed at 130C using an azeotropic distillation device with a Dean-Stark tube, and (S)-monochlorohydrin (2.59 g, 1.1 equivalents, >99%ee) was added dropwise under reflux such that the amount of the (S)-monochlorohydrin present in the reaction solution would be not more than 0.1 equivalent (not more than 2.1 mmol) relative to the amount of 2-bromo-4'-chloroacetophenone to be used (21.2 mmol), while analyzing the progress of the reaction by GC. After confirmation of the completion of the azeotropic distillation, the reaction mixture was cooled and washed with 10% aqueous sodium hydrogen carbonate solution and 10% brine. The solvent was evaporated under reduced pressure to give (4S)-trans-,cis-2-(4-chlorophenyl)-2-bromomethyl-4-chloromethyl-1,3-dioxolane (6.56 g, >99%ee). Here, the content percentage of (4S)-trans-,cis-2-(4-chlorophenyl)-2-chloromethyl-4-chloromethyl-1,3-dioxolane halogen-exchanged with a chlorine atom was 0.09%. Examples 30 to 41 Synthesis of (4S)-trans-cis-2-aryl-2-bromomethyl-4-chloromethyl-1,3-dioxolane suppressing halogen exchange In Examples 30 to 41, reactions were performed according to Example 23 and using aryl(bromomethyl)ketones (halogen-exchanged compound content<0.1%) shown in Table 7 and Table 8. The results are shown in Table 9 and Table 10 together with Example 23.
  • 6
  • [ 28179-33-1 ]
  • [ 39809-25-1 ]
  • 3-(4-hydroxy-3-(hydroxymethyl)butyl)-6-(4-phenoxyphenyl)-3,5-dihydro-9H-imidazo[1,2-a]purin-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% General procedure: To a suspension of penciclovir (6) or hydroxybutylguanine (7)(0.2 g, 0.8 mmol or 0.9 mmol, respectively) in dry dimethylformamide(16 mL), sodium hydride (60% suspension in mineral oil, 1.2 eq.) wasadded and the reaction stirred at room temperature (21 C) for 1.5 h.Bromoketone (8) (1.3 eq.) was then added and the reaction stirred for6 h. Aqueous ammonia (25% solution 5 mL) was added to quench thereaction, which was concentrated under reduced pressure and the residualoil purified by flash column chromatography using gradientelution (CH2Cl2-MeOH). The obtained products were recrystallisedfrom a mixture of CH2Cl2 and MeOH.
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