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Chemical Structure| 1016736-70-1 Chemical Structure| 1016736-70-1

Structure of 1016736-70-1

Chemical Structure| 1016736-70-1

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Product Details of [ 1016736-70-1 ]

CAS No. :1016736-70-1
Formula : C9H8BrNO
M.W : 226.07
SMILES Code : N#CCCOC1=CC=CC(Br)=C1
MDL No. :MFCD09932344

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Application In Synthesis of [ 1016736-70-1 ]

* 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 [ 1016736-70-1 ]

[ 1016736-70-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1016736-70-1 ]
  • [ 18442-22-3 ]
  • 5-bromo-2,3-dihydro-4H-chromen-4-one [ No CAS ]
  • 2
  • [ 1493-13-6 ]
  • [ 1016736-70-1 ]
  • [ 18442-22-3 ]
  • 5-bromo-2,3-dihydro-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a 25 mL 2-necked round-bottomed flask, equipped with thermocouple and nitrogen inlet, was charged 3-aryloxypropanenitriles 2a-2j (12.6 mmol) in 5 equiv of TFA(4.86 mL, 63.0 mmol) solution. To the resulting solution was slowly added 1.5 equiv of TfOH (1.67 mL, 17.7 mmol) at 0-5 C. The resulting solution was stirred at 0 C for 5 h, and then at ambient temperature for 16-24 h until the conversion of the reaction was >99%. The reaction mixture was cooled to 0 C. Then, 2 equiv of water (0.41 mL, 25.2 mmol) was added dropwise at 0-10 C. The resulting solution was stirred at room temperature for 1-5 h. The reaction mixture was transferred to a separation funnel and diluted with toluene (20 mL) and water (10 mL). After phase separation, the aqueous layer was extracted with toluene (6 mL × 1). The combined organic layers were washed with water (9 mL × 1) and concentrated. The pure 4-chromanones 3a, 3b, 3d, 3f, 3h, and 3i obtained by crystallization of their corresponding crude products in isopropanol (IPA) and the pure chromanones 3c, 3-4e, 3g and 3j were obtained by Biotage chromatographic purification (EtOAc/hexanes from 10% to 80%).
  • 3
  • [ 1016736-70-1 ]
  • [ 18442-22-3 ]
 

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