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Chemical Structure| 127971-97-5 Chemical Structure| 127971-97-5

Structure of 127971-97-5

Chemical Structure| 127971-97-5

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Product Details of [ 127971-97-5 ]

CAS No. :127971-97-5
Formula : C8H6BrNO5
M.W : 276.04
SMILES Code : O=C(O)C1=C(Br)C=CC(OC)=C1[N+]([O-])=O
MDL No. :MFCD14525762
InChI Key :GDQNQIOGEJXLHT-UHFFFAOYSA-N
Pubchem ID :14631586

Safety of [ 127971-97-5 ]

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

Application In Synthesis of [ 127971-97-5 ]

* 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 [ 127971-97-5 ]

[ 127971-97-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 4920-80-3 ]
  • [ 127971-97-5 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 2 h; Step A:; To a mixture of 3-methoxy-2-nitrobenzoic acid (2.5 g, 12.7 mmol) and silver sulfate (2.0 g, 6.4 mmol) in concd sulfuric acid (50 mL) was added bromine (2.03 g, 12.7 mmol), then the reaction mixture was stirred at room temperature in the dark for 2 h. Water was then added, and the resulting precipitate was collected. The solid was dissolved in acetone and the residue was filtered off. The filtrate was dried (MgSO4), filtered and concentrated to afford the brominated product (2.64 g, 75percent) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 14.50 (br s, 1H), 7.92 (d, J=9.0 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 3.93 (s, 3H).
71.8% at 0℃; for 2 h; Darkness To a suspended solution of 3-methoxy-2-nitrobenzoic acid (22.96 g, 116.5 mmol, 1.0 eq) in con. H2S04 (450 mL) was added Br2 (18.65 g, 116.5 mmol, 1.0 eq) at 0 °C, after the mixture stirred in dark at that temperature for 2 h, poured into ice (1350 mL), then warmed to rt and filtered and washed withwater (lOOmL x 2) to provide 6-bromo-3-methoxy-2-nitrobenzoic acid as a yellow solid (23.1 g, 71.8percent).
References: [1] Patent: US2006/183769, 2006, A1, . Location in patent: Page/Page column 41-42.
[2] Patent: WO2018/35061, 2018, A1, . Location in patent: Paragraph 0423.
[3] Journal of Organic Chemistry, 1990, vol. 55, # 15, p. 4581 - 4585.
  • 2
  • [ 4920-80-3 ]
  • [ 127971-97-5 ]
References: [1] Organic Letters, 2018, vol. 20, # 16, p. 5058 - 5061.
  • 3
  • [ 5345-42-6 ]
  • [ 127971-97-5 ]
References: [1] Organic Letters, 2018, vol. 20, # 16, p. 5058 - 5061.
 

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