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Chemical Structure| 7697-26-9 Chemical Structure| 7697-26-9

Structure of 7697-26-9

Chemical Structure| 7697-26-9

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CAS No.: 7697-26-9

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Product Details of [ 7697-26-9 ]

CAS No. :7697-26-9
Formula : C8H7BrO2
M.W : 215.04
SMILES Code : C1=C(C=CC(=C1Br)C)C(O)=O
MDL No. :MFCD00002488
Boiling Point : No data available
InChI Key :ZFJOMUKPDWNRFI-UHFFFAOYSA-N
Pubchem ID :82130

Safety of [ 7697-26-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H315-H319-H335
Precautionary Statements:P261-P301+P310-P305+P351+P338
Class:6.1
UN#:2811
Packing Group:Ⅲ

Application In Synthesis of [ 7697-26-9 ]

* 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.

  • Upstream synthesis route of [ 7697-26-9 ]
  • Downstream synthetic route of [ 7697-26-9 ]

[ 7697-26-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 7697-26-9 ]
  • [ 89892-39-7 ]
References: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 644 - 651.
  • 2
  • [ 7697-26-9 ]
  • [ 876189-18-3 ]
References: [1] Patent: WO2014/144380, 2014, A1, .
  • 3
  • [ 121-43-7 ]
  • [ 7697-26-9 ]
  • [ 170230-88-3 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere
Stage #2: at -78 - 20℃; Inert atmosphere		 3-Bromo-4-methylbenzoic acid (11.00 g, 51.2 mmol) was dissolved in anhydrous THF (150 ml) under argon in a 500 ml 3-necked round bottom flask fitted with two dropping funnels and argon inlet. The stirred solution was cooled to -78°C and n-BuLi (1.6M in hexane, 60.7 ml, 97.0 mmol) was added drop wise from a dropping funnel (during lh). After completion of the addition, the solution was stirred at -78°C for another 1 h. To this, B(OMe)3 (17.7 ml, 159.0 mmol) was added slowly from a second dropping funnel. The mixture was stirred 1 h at -78°C and then warmed up to room temperature overnight. The solvent was evaporated under reduced pressure. The crude product was dissolved in ether and poured into aqueous HCI (IN). The mixture was extracted with ether (3 X 150 ml), and the combined organic layers were washed with brine, dried over anhydrous MgS04, filtered, and evaporated to dryness. The crude product was purified using an ISCO system (220 g silica column, hexane/EtOAc gradient and later DCM/MeOH gradient). The impurities washed off in hexane/EtOAc and the pure product eluted in MeOH/DCM (5:95) solvent mixture to give 3.3 g (33 percent yield) of pure SKC-01-126, 1H NMR (400 MHz, Acetone-d6) δ 12.10 (br s, 1H), 8.16 (s, 1H), 7.90 - 7.63 (m, 1H), 7.11 (d, J - 7.9 Hz, 1H), 2.42 (s, 3H).
References: [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 8, p. 1492 - 1495.
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3909 - 3913[3] Angew. Chem., 2016, p. 3977 - 3981,5.
[4] Patent: WO2014/144380, 2014, A1, . Location in patent: Page/Page column 109; 110.
  • 4
  • [ 7697-26-9 ]
  • [ 956697-53-3 ]
References: [1] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684.
 

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