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Chemical Structure| 453566-15-9 Chemical Structure| 453566-15-9

Structure of 453566-15-9

Chemical Structure| 453566-15-9

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Product Details of [ 453566-15-9 ]

CAS No. :453566-15-9
Formula : C9H6BrNO2
M.W : 240.05
SMILES Code : COC(=O)C1=CC(Br)=CC(=C1)C#N
MDL No. :MFCD16620379
InChI Key :DNNTVDNUUQKALF-UHFFFAOYSA-N
Pubchem ID :21942615

Safety of [ 453566-15-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302+H312-H315-H319-H331-H335
Precautionary Statements:P261-P280-P305+P351+P338-P311
Class:6.1
UN#:3439
Packing Group:

Application In Synthesis of [ 453566-15-9 ]

* 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 [ 453566-15-9 ]
  • Downstream synthetic route of [ 453566-15-9 ]

[ 453566-15-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 453566-15-9 ]
  • [ 453566-14-8 ]
YieldReaction ConditionsOperation in experiment
85% With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; To methyl 3-bromo-5-carbamoyl-benzoate (2.8 g, 10.8 mmol, 1.0 eq) was added POCI3 (30 mL) and the reaction heated at 100 °C overnight. The POCI3 was removed under reduced pressure, water was added and the aqueous layer extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo to afford a crude residue which was purified by column chromatography (petroleum ethenEtOAc, 20:1 ) to give methyl 3-bromo-5-cyano-benzoate (2.5 g, 96 percent). This material was dissolved in THF (30 mL) and LiOH.H20 (1.7 g, 41.6 mmol, 1.54 eq) and H20 (10 mL) were added. The mixture was stirred at room temperature overnight. The THF was removed under reduced pressure and the aqueous phase acidified with diluted HC1 and extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2C12: MeOH, 50: 1) to give the title compound as a white solid (2 g, 85 percent).LC-MS: m z 248.0, 249.9 [M+Na1H NMR (400 MHZ, DMSO) δ 13.67 (br s, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 8.24 (s, 1H).
References: [1] Patent: WO2013/37705, 2013, A2, . Location in patent: Page/Page column 139.
 

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