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Chemical Structure| 202808-22-8 Chemical Structure| 202808-22-8

Structure of 202808-22-8

Chemical Structure| 202808-22-8

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Product Details of [ 202808-22-8 ]

CAS No. :202808-22-8
Formula : C7H3BrClNO3
M.W : 264.46
SMILES Code : O=CC1=CC(Br)=C(Cl)C=C1[N+]([O-])=O
English Name :5-Bromo-4-chloro-2-nitrobenzaldehyde
MDL No. :MFCD26398731

Safety of [ 202808-22-8 ]

Application In Synthesis of [ 202808-22-8 ]

* 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 [ 202808-22-8 ]

[ 202808-22-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1467-84-1 ]
  • [ 202808-22-8 ]
  • [ 2785398-40-3 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: ((1r,4r)-4-aminocyclohexyl)methanol; 5-bromo-4-chloro-2-nitrobenzaldehyde In isopropanol at 80℃; for 3h; Inert atmosphere; Stage #2: With tributylphosphine In isopropanol at 80℃; for 9h; Inert atmosphere; 2 Step 2 - ((1R,4r)-4-(5-bromo-6-chloro-2H-indazol-2-yl)cyclohexyl)methanol A solution of 5-bromo-4-chloro-2-nitro-benzaldehyde (650 mg, 2.46 mmol) and (4- aminocyclohexyl) methanol (317 mg, 2.46 mmol, CAS1467-84-1) in IPA (7 mL) was stirred at 80 °C for 3 hours. Then tributylphosphane (1.49 g, 7.37 mmol) was added and the mixture was stirred at 80 °C for 9 hours. On completion, the reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate = 10/1 to 1/1) to give the title compound (600 mg, 70% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.91 (s, 1H), 7.86 (s, 1H), 4.38 (m, 1H), 3.57 (m, 2H), 2.42 - 2.28 (m, 2H), 2.10 - 2.03 (m, 2H), 2.02 - 1.90 (m, 2H), 1.68 (m, 1H), 1.26 (m, 2H); LC-MS (ESI+) m/z 343.9 (M+H)+
70% Stage #1: ((1r,4r)-4-aminocyclohexyl)methanol; 5-bromo-4-chloro-2-nitrobenzaldehyde In isopropanol at 80℃; for 3h; Inert atmosphere; Stage #2: With tributylphosphine In isopropanol at 80℃; for 9h; Inert atmosphere; 2 Step 2 - ((1R,4r)-4-(5-bromo-6-chloro-2H-indazol-2-yl)cyclohexyl)methanol A solution of 5-bromo-4-chloro-2-nitro-benzaldehyde (650 mg, 2.46 mmol) and (4- aminocyclohexyl) methanol (317 mg, 2.46 mmol, CAS1467-84-1) in IPA (7 mL) was stirred at 80 °C for 3 hours. Then tributylphosphane (1.49 g, 7.37 mmol) was added and the mixture was stirred at 80 °C for 9 hours. On completion, the reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate = 10/1 to 1/1) to give the title compound (600 mg, 70% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.91 (s, 1H), 7.86 (s, 1H), 4.38 (m, 1H), 3.57 (m, 2H), 2.42 - 2.28 (m, 2H), 2.10 - 2.03 (m, 2H), 2.02 - 1.90 (m, 2H), 1.68 (m, 1H), 1.26 (m, 2H); LC-MS (ESI+) m/z 343.9 (M+H)+
 

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