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Chemical Structure| 35450-37-4 Chemical Structure| 35450-37-4

Structure of 35450-37-4

Chemical Structure| 35450-37-4

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Product Details of [ 35450-37-4 ]

CAS No. :35450-37-4
Formula : C9H9BrO3
M.W : 245.07
SMILES Code : O=C(OC)C1=CC=C(OC)C(Br)=C1
MDL No. :MFCD00210463
InChI Key :ZREVPFANJBZHEU-UHFFFAOYSA-N
Pubchem ID :611662

Safety of [ 35450-37-4 ]

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

Application In Synthesis of [ 35450-37-4 ]

* 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 [ 35450-37-4 ]
  • Downstream synthetic route of [ 35450-37-4 ]

[ 35450-37-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 35450-37-4 ]
  • [ 25978-74-9 ]
YieldReaction ConditionsOperation in experiment
79% With copper(l) cyanide In N,N-dimethyl-formamide at 140℃; for 6 h; To a solution of compound y (1.1 g, 4.4 mol) in dimethylformamide (10 mL) was added cuprous cyanide (1.2 g, 13.2 mmol). And the mixture was heated to 140 ° C for 6 hours. The reaction system was cooled and then ethyl acetate (25 mL) was added. The extracted organic phase was washed with saturated brine and the concentrated residue was dried and concentrated by flash column chromatography (petroleum ether: ethyl acetate = 10: 1) to give a white solid Compound z: Methyl 3-cyano-4-methoxybenzoate (662 mg, yield 79percent).
References: [1] Patent: CN106146504, 2016, A, . Location in patent: Paragraph 0219; 0220; 0221; 0224; 0225.
  • 2
  • [ 35450-37-4 ]
  • [ 25978-74-9 ]
YieldReaction ConditionsOperation in experiment
79% at 140℃; for 6 h; To a solution of Compound d' (1.1 g, 4.4 mol) dissolved in dimethyl formamide (10 mL), cuprous cyanide (1.2 g, 13.22 mmol) was added, heated to 140°C, and stirred for 6 hrs. The reaction system was cooled, added with ethyl acetate (25 mL), and extracted. Then, the organic phase was washed with saturated saline, dried and concentrated. The resulting residue was separated by flash column chromatography (petroleum ether:ethyl acetate=10:1), to obtain Compound e': methyl 3-cyano-4-methoxybenzoate as a white solid (662 mg, yield 79percent).
References: [1] Patent: EP3284743, 2018, A1, . Location in patent: Paragraph 0155.
[2] Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277.
  • 3
  • [ 35450-37-4 ]
  • [ 38493-59-3 ]
YieldReaction ConditionsOperation in experiment
98% With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - 0℃; for 1 h; Inert atmosphere To a solution of methyl 3-bromo-4-methoxybenzoate (12, 2.00 g, 8.16 mmol) in THF (20 mL) was added DIBAL–H (1.00 M in hexane, 20.4 mL) at −78 °C. The mixture was stirred at −78 °C for 30 min and 0 °C for 30 min. To the reaction mixture at −78 °C was added methanol (10 mL) dropwisely followed by saturated aqueous Rochelle salt solution (16 mL) and EtOAc (20 mL). After being stirred at room temperature for 2 h, the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, and then concentrated in vacuo. Purification on silica gel column chromatography (hexane/EtOAc=2:1) gave 13 (1.73 g, 7.96 mmol, 98percent) as a colorless solid; Rf 0.17 (hexane/EtOAc=3:1); 1H NMR (300 MHz, CDCl3) δ 7.57 (1H, d, J=2.2 Hz, H18), 7.27 (1H, dd, J=8.6, 2.2 Hz, H15), 6.88 (1H, d, J=8.6 Hz, H16), 4.61 (2H, s, H13), 3.90 (3H, s, OMe); 13C NMR (75 MHz, CDCl3) δ 55.5, 134.6, 132.4, 112.0, 111.8, 64.4, 56.4; EIMS (m/z) calcd for C8H9BrO2 [M]+ 215.98, found 216.05
References: [1] Tetrahedron, 2013, vol. 69, # 13, p. 2807 - 2815.
 

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