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Chemical Structure| 191602-42-3 Chemical Structure| 191602-42-3

Structure of 191602-42-3

Chemical Structure| 191602-42-3

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Product Details of [ 191602-42-3 ]

CAS No. :191602-42-3
Formula : C9H10BrNO3
M.W : 260.09
SMILES Code : O=[N+](C1=CC=C(OC(C)C)C(Br)=C1)[O-]
MDL No. :MFCD12547884

Safety of [ 191602-42-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 191602-42-3 ]

* 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 [ 191602-42-3 ]

[ 191602-42-3 ] Synthesis Path-Downstream   1~2

  • 2
  • [ 5847-59-6 ]
  • [ 67-63-0 ]
  • [ 191602-42-3 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; Adapting literature procedures (Swamy, et al., Chem. Rev., 2009, 109, 2551-2651; Lepore and He, J. Org. Chem., 2003, 68, 8261-8263), 2-bromo-l-isopropoxy-4-nitro-benzene (43a) was prepared by reacting a solution of commercial <strong>[5847-59-6]2-bromo-4-nitro-phenol</strong> (654 mg, 3.0 mmol), 2-propanol (iPrOH) (458 [iL, 360 mg, 6.0 mmol), and triphenylphosphine (PPh3) (2.4 g, 9.0 mmol) in anhydrous tetrahydrofuran (THF) (10 mL) at 0C (ice bath) with neat diisopropylazodicarboxylate (DIAD) (1.77 mL, 1.82 g, 9.0 mmol). The reaction mixture was stirred for overnight with gradual warming to room temperature. Extractive basic aqueous work-up with ethyl acetate and purification by silica gel chromatography using an ethyl acetate (EtOAc)/hexane mixture (EtOAc/hexane = 1 :4, v/v) provided 800 mg (-quant, yield) of the target compound (43a) as a yellow oil that solidified to a yellow solid upon standing. Rf. -0.79 (EtOAc/hexane = 1 : 1, v/v). 1H NMR (300 MHz, CDC13): delta 8.45 (d, J= 2.7 Hz, 1H), 8.17 (dd, J= 9.3, 2.7 Hz, 1H), 6.93 (d, J= 9.0 Hz, 1H), 4.71 (septet, J= 6.0 Hz, 1H), 1.44 (d, J= 6.3 Hz, 6H) ppm. LC/MS: Rt = 3.037 min; -76% purity by AUC at lambda = 254 nm; ESI (pos.) mlz = 260.40 (M+H+)+.
 

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