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Chemical Structure| 99821-59-7 Chemical Structure| 99821-59-7

Structure of 99821-59-7

Chemical Structure| 99821-59-7

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Product Details of [ 99821-59-7 ]

CAS No. :99821-59-7
Formula : C9H8BrNO3
M.W : 258.07
SMILES Code : CC(C1=CC(CBr)=CC=C1[N+]([O-])=O)=O

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Application In Synthesis of [ 99821-59-7 ]

* 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 [ 99821-59-7 ]

[ 99821-59-7 ] Synthesis Path-Downstream   1~2

  • 1
  • concentrated H2 SO4 [ No CAS ]
  • [ 3113-72-2 ]
  • [ 69976-70-1 ]
  • [ 105-53-3 ]
  • [ 99821-59-7 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; magnesium; dibenzoyl peroxide; In tetrachloromethane; CCl; thionyl chloride; ethanol; chloroform; water; acetic acid; chlorobenzene; Example 1 Synthesis of Photocleavable Agents Five grams or 27.6 mmol of 5-methyl-2-nitrobenzoic acid (FIG. 5, compound "6"; Aldrich Chemical; Milwaukee, Wis.) was added in small portions to 10 ml (16.4 g or 148 mmol) of thionyl chloride with stirring. The mixture was stirred at room temperature for 10 hours. Excess of thionyl chloride was removed by vacuum to give the acid chloride ("7"). Magnesium turnings (1.07 g or 44.2 mmol), absolute ethanol (6 ml), chlorobenzene (8 ml), and 0.1 ml of dry CCl4, were refluxed until most of the magnesium reacted. A solution of diethyl malonate (4.82 g or mmol) in 10 ml of chlorobenzene was added followed by the addition of the acid chloride (5.49 g) in 10 ml of chlorobenzene. The reaction mixture stirred for 1 hour and 1.7 ml of concentrated H2 SO4 in 17 ml of H2 O was added, stirred for additional 15 minutes. 20 ml of chloroform was added and the layers separated. The aqueous layer was extracted three times with 10 ml and the extracts were combined, dried and evaporated to dryness. Residue was dissolved in 8.25 mls of acetic acid. 5.4 ml of H2 O and 1 ml of concentrated H2 SO4 were added, the mixture was refluxed for 6 hours, neutralized with aqueous Na2 CO3 and extracted three times with 20 ml of CHCl3. Extracts were combined, dried and solvents removed by vacuum. Residue was crystallized from 70% ethanol to produce 4.46 g, or about 81%, of <strong>[69976-70-1]5-methyl-2-nitroacetophenone</strong>. <strong>[69976-70-1]5-methyl-2-nitroacetophenone</strong> (3.51 g or 19.6 mmol), N-bromosuccinimide (3.66 g or 20.6 mmol), and benzoyl peroxide (46 mg or 0.01 eq) were refluxed in 20 ml of CCl, for 5 hours. The reaction mixture was filtered, the filtrate concentrated and crystallized from CCl4 to produce 3.64 g (72%) of 5-bromomethyl-2-nitroacetophenone ("8").
 

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