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Chemical Structure| 33295-53-3 Chemical Structure| 33295-53-3

Structure of 33295-53-3

Chemical Structure| 33295-53-3

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Product Details of [ 33295-53-3 ]

CAS No. :33295-53-3
Formula : C11H9BrO
M.W : 237.09
SMILES Code : COC1=C2C=C(Br)C=CC2=CC=C1
MDL No. :MFCD17012269
InChI Key :BTPIORDWKIZDNM-UHFFFAOYSA-N
Pubchem ID :21865983

Safety of [ 33295-53-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 33295-53-3 ]

* 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 [ 33295-53-3 ]

[ 33295-53-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 91270-69-8 ]
  • [ 77-78-1 ]
  • [ 33295-53-3 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate;tetrabutylammomium bromide; In acetonitrile; for 2.75h;Heating / reflux; Preparation of 7-Bromo-1-methoxynaphthalene. [CHEMMOL-00140] [0466] A slurry of <strong>[91270-69-8]7-bromo-1-naphthol</strong> (8.89 g, 39.9 mmol), potassium carbonate (8.26 g, 59.8 mmol), dimethyl sulfate (5.66 mL, 59.8 mmol) and tetrabutylammonium bromide (0.085 g, 0.264 mmol) in acetonitrile (160 mL) was heated at reflux for 2 h 45 min. The reaction was cooled to room temperature, and water was added (200 mL). The mixture was then extracted (1.x.100, 1.x.40 mL) with CH2Cl2. The combined organic layers were washed (1.x.40 mL) with saturated aqueous NaHCO3 solution, dried over MgSO4, and concentrated. The residue was purified by medium pressure chromatography (100percent hexanes) to give the intermediate title compound as a yellow oil (8.42 g, 89percent). FDMS m/e=236 M+.
  • 2
  • [ 91270-69-8 ]
  • [ 74-88-4 ]
  • [ 33295-53-3 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate; In acetone; at 65℃; for 2h; Step E: Potassium carbonate (3.3 g, 23.9 mmol) and methyl iodide (1.5 ml, 23.9 mmol) were added to a solution of the product from Step D (2.7 g, 11.9 mmol) in acetone (40 ml) at room temperature and the mixture was stirred at 65° C. for 2 hours. The solids were filtered, rinsed with ethyl acetate and the filtrate was evaporated. The residue was dissolved in ethyl acetate and washed with water twice. The aqueous layers were extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulfate to give 7-bromo-1-methoxynaphthalene (2.5 g, 88percent) after chromatography (19:1 heptane/ethyl acetate): 1H NMR (300 MHz, CDCl3) delta 8.49 (d, J=2.1 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.59 (dd, J=8.7, 2.1 Hz, 1H), 7.39-7.43 (m, 2H), 6.85 (dd, J=5.4, 3.0 Hz, 1H), 3.15 (s, 3H).
 

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