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Chemical Structure| 143888-84-0 Chemical Structure| 143888-84-0

Structure of 143888-84-0

Chemical Structure| 143888-84-0

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Product Details of [ 143888-84-0 ]

CAS No. :143888-84-0
Formula : C7H6BrClO
M.W : 221.48
SMILES Code : ClC1=CC=C(C(Br)=C1)CO
MDL No. :MFCD09056765

Safety of [ 143888-84-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 143888-84-0 ]

* 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 [ 143888-84-0 ]

[ 143888-84-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 57381-62-1 ]
  • [ 143888-84-0 ]
YieldReaction ConditionsOperation in experiment
A 1.0 M solution of diisobutylaluminum hydride in toluene (43 ml_, 0.043 mol) was added slowly drop-wise to a -78 °C solution of <strong>[57381-62-1]2-bromo-4-chloro-benzoic acid methyl ester</strong> (10.57 g, 0.042 mol) in toluene (50 ml_) and hexanes (425 ml_). The reaction mixture was stirred at -78 °C for 1.5 hours. After this time, a white solid had precipitated out of solution. The reaction mixture was quenched at -78 °C with ethyl acetate (100 ml_). Saturated aqueous sodium potassium tartrate was added, and the reaction mixture was warmed to room temperature. The organic phase was separated, dried over Na2SO4, filtered, and concentrated to a clear oil. TLC (30percent ethyl acetate/hexanes) and 1H NMR revealed a mixture with unreacted 2-bromo-4- chloro-benzoic acid methyl ester as the major component. The crude material was dissolved in toluene (300 ml_), and the resulting solution was cooled to -78 °C. A 1.0 M solution of diisobutylaluminum hydride in toluene (55 ml_, 0.055 mol) was added slowly drop-wise to the reaction mixture. The reaction mixture was warmed to - 45 °C and stirred at this temperature for 35 minutes. At this time, TLC (10percent ethyl acetate/hexanes) indicated nearly complete consumption of the starting material. The reaction mixture was quenched at -45 °C with ethyl acetate. Saturated aqueous sodium potassium tartrate was added, and the reaction mixture was warmed to room temperature and stirred at room temperature for 1 hour. The organic phase was separated, dried over Na2SO4, and concentrated to a yellow oil. A solution of this crude product and dichloromethane (200 mL) was evaporated onto silica gel, and the dry silica gel-supported product was loaded onto a 120 g silica gel column. Flash chromatography was carried out using an ISCO purification system (95:5 hexanes- ethyl acetate ramped to 4:1 hexanes-ethyl acetate). (2-Bromo-4-chloro-phenyl)- methanol was isolated as 5.57 g (60percent yield) of a white solid.
  • 2
  • [ 27139-97-5 ]
  • [ 143888-84-0 ]
 

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