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[ CAS No. 155586-39-3 ] {[proInfo.proName]}

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Chemical Structure| 155586-39-3
Chemical Structure| 155586-39-3
Structure of 155586-39-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 155586-39-3 ]

CAS No. :155586-39-3 MDL No. :MFCD02684301
Formula : C11H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 225.24 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 155586-39-3 ]

* 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.

  • Downstream synthetic route of [ 155586-39-3 ]

[ 155586-39-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 2150-37-0 ]
  • [ 6638-79-5 ]
  • [ 155586-39-3 ]
YieldReaction ConditionsOperation in experiment
98% With isopropylmagnesium chloride In tetrahydrofuran at -10℃; for 0.333333h;
  • 2
  • [ 111-25-1 ]
  • [ 155586-39-3 ]
  • [ 39192-51-3 ]
  • 3
  • [ 695-96-5 ]
  • [ 155586-39-3 ]
  • [ 329944-55-0 ]
YieldReaction ConditionsOperation in experiment
20% Stage #1: 2-bromo-4-chlorophenol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: (3,5-dimethoxyphenyl)-N-methoxy-N-methylcarboxamide In tetrahydrofuran; hexane at -78 - 20℃; for 15.25h;
20% Stage #1: 2-bromo-4-chlorophenol With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.08333h; Cooling with acetone-dry ice; Stage #2: (3,5-dimethoxyphenyl)-N-methoxy-N-methylcarboxamide In tetrahydrofuran; hexanes at -78 - 20℃; for 15.3167h; 197.B A solution of 2-bromo-4-chlorophenol (0.830 g, 4.0 mmol) in 20 mL of THF was cooled to -78 °C in a dry ice/acetone bath. n-Butyllithium (5.5 mL of a 1.6 M solution in hexanes, 8.8 mmol) was added dropwise over 5 min, and the resulting mixture was stirred at -78 °C for 1 h. A solution of 468 (0.901 g, 4.0 mmol) in 5 mL of THF was added dropwise over 4 min, and the resulting mixture was stirred at -78 °C for 1.25 h, then at room temperature for 14 h. The reaction mixture was poured into 50 mL of water and extracted with two 50-mL portions of EtOAc. The combined organic layers were then dried over MgSO4, filtered and concentrated in vacuo to give 1.193 g of a brown oil. Purification by flash chromatography using 10% EtOAc/hexanes as an eluant followed by crystallization from hot ether gave 469 as yellow crystals (0.234 g, 20%): 1H NMR (CDCl3, 300 MHz) δ 11.83 (s, 1 H), 7.62 (d, 1 H), 7.45 (dd, 1 H), 7.03 (d, 1 H), 6.76 (d, 2 H), 6.68 (t, 1 H), 3.84 (s, 6 H).
  • 4
  • [ 6638-79-5 ]
  • [ 1132-21-4 ]
  • [ 155586-39-3 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 3,5-dimethoxybenzoic acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; chemoselective reaction; General procedure for the synthesis of Weinreb amides General procedure: A. To a mixture of benzoic acid (50 mg, 0.41 mmol, 1 equiv), PPh3 (160 mg, 0.61 mmol, 1.5 equiv) and NBS (108.5 mg, 0.61 mmol, 1.5 equiv), CH2Cl2 (2 ml) was added and the reaction was stirred at 0 °C for 15 min. The reaction was brought to room temperature and N,O-dimethylhydroxylamine hydrochloride (59.5 mg, 0.61 mmol, 1.5 equiv) and Et3N (45.5 mg, 63 µl, 0.45 mmol, 1.1 equiv) were added and reaction was stirred for 1 h at room temperature. The reaction mixture was quenched with aqueous sodium bicarbonate solution and diluted with CH2Cl2. The bicarbonate washings were again extracted with CH2Cl2 and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. Column chromatography was performed using EtOAc/Petroleum ether (1:5).
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