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Chemical Structure| 13288-06-7

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Product Details of [ 13288-06-7 ]

CAS No. :13288-06-7
Formula : C8H8BrNO3
M.W : 246.06
SMILES Code : O=[N+](C1=CC=C(OCCBr)C=C1)[O-]
MDL No. :MFCD00031363
Boiling Point : No data available
InChI Key :YQWCBDNNEZHPMA-UHFFFAOYSA-N
Pubchem ID :235987

Safety of [ 13288-06-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 13288-06-7 ]

* 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 [ 13288-06-7 ]

[ 13288-06-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 16115-08-5 ]
  • [ 13288-06-7 ]
  • [ 1029804-54-3 ]
YieldReaction ConditionsOperation in experiment
11% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; Reference Example 38; 2,4-Dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridine; A mixture of <strong>[16115-08-5]2-hydroxy-4,6-dimethylpyridine</strong> (1.7 g, 13.8 mmol), potassium carbonate (3.82 g, 27.6 mmol) and 1-(2-bromo-ethoxy)-4-nitro-benzene (4.0 g, 16.6 mmol) in DMF (30 mL) was heated to 120° C. and maintained for 15 h. The mixture was cooled to ambient temperature, filtered and concentrated to give a residue which was purified by column chromatography using 4percent ethyl acetate/petroleum ether as eluent to afford 2,4-dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridine as yellow solid (530 mg, 11percent).
11% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 15.0h; Reference Example 104: 2, 4-Dimethyl-6-f2-(4-nitro-phenoxy)-ethoxy)pyridine. A mixture of 2-hydroxy-4,6-dimethyl pyridine (1.7 g, 13.8 mmol), potassium carbonate (3.82 g, 27.6 mmol) and l-(2-bromo-ethoxy)-4-nitro-benzene (4.0 g, 16.6 mmol) in DMF (30 mL) was heated to 120 °C and maintained for 15 h. The mixture was cooled to ambient temperature, filtered and concentrated to give a residue which was purified by column chromatography using 4percent ethyl acetate/petroleum ether as eluent to afford 2,4-dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridine as yellow solid (530 mg, 11percent)
  • 2
  • [ 495-78-3 ]
  • [ 13288-06-7 ]
  • [ 872450-82-3 ]
YieldReaction ConditionsOperation in experiment
23% 25 g (0.15 M) of 2-hydroxyphenylpropanoic acid and 16.9 g (0.12 M) ofpotassium hydroxide are added to a mixture of 150 ml of methanol and 20 ml of dimethylformamide in a 1000 ml reactor. After stirring for 10 minutes, 30 g (0.15 M) of 2-(4-nitrophenoxy)ethyl bromide are added and the reaction medium is then refluxed for 24 hours with stirring. The methanol is evaporated off and the residue is taken up in water. The aqueous phase obtained is first washed with ethyl acetate and then acidified with dilute aqueous hydrochloric acid and extracted with ethyl acetate.The organic phase is evaporated under vacuum and the residue obtained is purified by chromatography on silica, with a dichloromethane/methanol mixture (95/5) as eluent. After concentrating, 9 g of a beige-coloured solid are obtained (yield: 23%).NMR(5 in ppm, DMSO, 200 MHz): 2.33 (t, 2H); 2.58 (t, 2H); 4.20 (s, 2H); 4.35 (s, 2H); 6.8 (multiple., 6H); 8.06 (d, 2H).
  • 3
  • [ 110-91-8 ]
  • [ 13288-06-7 ]
  • [ 65300-53-0 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate; In acetonitrile; at 80℃; for 4h; Into a 30 mL vial, [A] l-(2-Bromo-ethoxy)-4-nitro-benzene (5.00 g, 0.0203 mol), Morpholine (3.54 mL, 0.0406 mol) , Acetonitrile (15.0 mL, 0.287 mol) and Potassium carbonate (5.62 g, 0.0406 mol) were added. The reaction was heated at 80 0C for 4 hours. The reaction was partitioned with water (250 mL). The solid was filtered and washed with water. The resulting solid was dried under vacuum overnight to give 4-[2-(4- Nitrophenoxy)-ethyl] -morpholine as an off-white solid (4.3Og, 84%). NMR 1H (DSMO- d6)- 8.20 (d, IH, J= 9.34 Hz), 7.17 (d, 2H, J= 9.34 Hz), 4.24 (t, 2H, J= 5.65 Hz), 3.57 (t, 4H, J= 4.60 Hz), 2.72 (t, 2H, J= 4.68 Hz), 2.47 (t, 4H, J= 4.52 Hz),
900 mg With potassium carbonate; In acetonitrile; for 3h;Reflux; Compound 8-c (1.0 g, 4.08 mmol) and morpholine (702 mg, 8.16 mmol) were dissolved in acetonitrile (5 mL), potassium carbonate (1.2 g, 8.16 mmol) was added. The mixture was refluxed for 3 hours, and then cooled to room temperature, after filtration, the filter cake was washed with ethyl acetate (30 mL). The filtrate was concentrated under reduced pressure, the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL×3). The organic layers were combined and washed with water (50 mL×3) and saturated brine (50 mL) in sequence. After dried over anhydrous sodium sulfate, the mixture was filtrated, and the filtrate was concentrated in vacuum to give light yellow solid 8-b (900 mg), which was used directly for the next step without further purification.
 

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