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[ CAS No. 1214334-70-9 ]

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Chemical Structure| 1214334-70-9
Chemical Structure| 1214334-70-9
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CAS No. :1214334-70-9 MDL No. :MFCD13185810
Formula : C7H6BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :232.03 g/mol Pubchem ID :53485621
Synonyms :

Safety of [ 1214334-70-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1214334-70-9 ]

  • Upstream synthesis route of [ 1214334-70-9 ]
  • Downstream synthetic route of [ 1214334-70-9 ]

[ 1214334-70-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 959958-25-9 ]
  • [ 124-41-4 ]
  • [ 1214334-70-9 ]
YieldReaction ConditionsOperation in experiment
94% at 20 - 80℃; for 42 h; 5-bromo-6-methoxypicolinic acid: A suspension of 5-bromo-6-chloropicolinic acid (15.0 g, 63.4 mmol, 1.0 equiv.) in MeOH (130 mL) at ambient temperature was treated with a 4.37 M sodium methoxide solution in MeOH (58.0 mL, 253 mmol, 4.0 equiv.). The resultant mixture was heated at 80 °C for 18 hours, resulting in a thick mixture. The reaction was diluted with MeOH (100 mL) and stirred at 80 °C for 24 hours. The reaction mixture was cooled to ambient temperature, acidified to pH=3 with concentrated aqueous HC1, diluted with water and extracted with EtOAc (three times). The combined organic layers were dried over MgSO4, filtered and concentrated to afford a residue that was co-evaporated with DCM/hexanes (1:1 mixture, 200 mL, three times) to afford 5-bromo-6-methoxypicolinic acid (13.9 g, 94percent) as a white solid. ‘H NMR (500 MHz, CDC13) 5 10.22 (br s, 1H), 8.06 (d, I = 7.7 Hz, 1H), 7.73 (d, I = 7.7 Hz, 1H), 4.10 (s, 3H). LCMS (ES-) [M-Hj+: 229.9/23 1.9.
Reference: [1] Patent: WO2016/201168, 2016, A1, . Location in patent: Paragraph 0174
  • 2
  • [ 185017-72-5 ]
  • [ 1214334-70-9 ]
Reference: [1] Patent: WO2011/48525, 2011, A1,
[2] Patent: WO2017/31325, 2017, A1,
  • 3
  • [ 1214334-70-9 ]
  • [ 74-88-4 ]
  • [ 1214329-07-3 ]
YieldReaction ConditionsOperation in experiment
94% With sodium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 16 h; To a solution of 5-bromo-6-methoxypicolinic acid (1) (1.0 g, 0.00431 mol) in DMF (10 mL, 10 vol), cooled to 0 °C was added Na2CO3 (456 mg, 0.00431 mol) and MeI (0.536 mL, 0.0086 mol) the mixture was stirred for16 h at room temperature. Water was added, extracted with ethyl acetate, dried and purified by column chromatography using a gradient of hexane-EtOAc (9:1-8:2) to give pure compound (2): Off white solid; yield: 94 percent, 1H NMR (500MHz, CDCl3) δ: 3.98 (s, 3H), 4.08 (s, 3H), 7.58 (d, 1H, Ar-H),7.98 (d, 1H, Ar-H): MS: m/z (percent) 247.6 [M+2], HPLC purity(99.52 percent).
Reference: [1] Asian Journal of Chemistry, 2015, vol. 27, # 12, p. 4579 - 4582
[2] Letters in Organic Chemistry, 2016, vol. 13, # 4, p. 249 - 254
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