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[ CAS No. 86232-28-2 ] {[proInfo.proName]}

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Chemical Structure| 86232-28-2
Chemical Structure| 86232-28-2
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Product Details of [ 86232-28-2 ]

CAS No. :86232-28-2 MDL No. :MFCD01743107
Formula : C9H9ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :FIRVUYUWCDJOMJ-UHFFFAOYSA-N
M.W : 200.62 Pubchem ID :4172275
Synonyms :

Safety of [ 86232-28-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 86232-28-2 ]

* 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 [ 86232-28-2 ]

[ 86232-28-2 ] Synthesis Path-Downstream   1~37

  • 2
  • [ 86232-28-2 ]
  • [ 86232-27-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; hydrazine hydrate 1) reflux, 2) reflux; Yield given. Multistep reaction;
  • 4
  • [ 86232-26-0 ]
  • [ 67-64-1 ]
  • [ 77-78-1 ]
  • [ 86232-28-2 ]
  • [ 86232-29-3 ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 11% With potassium carbonate In acetone for 5h; Heating;
  • 5
  • [ 86232-26-0 ]
  • [ 77-78-1 ]
  • [ 86232-28-2 ]
  • [ 86232-29-3 ]
YieldReaction ConditionsOperation in experiment
1: 11% 2: 75% With potassium carbonate In acetone for 5h; Heating;
  • 6
  • [ 86232-28-2 ]
  • [ 74-88-4 ]
  • [ 117052-18-3 ]
YieldReaction ConditionsOperation in experiment
With magnesium 2.) ether, benzene, reflux, 6 h; Yield given. Multistep reaction;
YieldReaction ConditionsOperation in experiment
5-Chlor-2-hydroxy-3-methoxy-benzaldehyd, Dimethylsulfat/wss. NaOH, 50grad;
  • 8
  • [ 7740-05-8 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 5 h, 2) reflux, 5 h 2: 75 percent / K2CO3 / acetone / 5 h / Heating
  • 9
  • [ 86232-28-2 ]
  • [ 87964-82-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating
Multi-step reaction with 3 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating
  • 10
  • [ 86232-28-2 ]
  • [ 86232-33-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating
  • 11
  • [ 86232-28-2 ]
  • [ 86232-31-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation
  • 12
  • [ 86232-28-2 ]
  • [ 86232-37-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C
Multi-step reaction with 3 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C
  • 13
  • [ 86232-28-2 ]
  • [ 86232-47-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating
Multi-step reaction with 5 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating
Multi-step reaction with 5 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating

  • 14
  • [ 86232-28-2 ]
  • [ 86232-49-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane

  • 15
  • [ 86232-28-2 ]
  • [ 86232-41-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C
Multi-step reaction with 4 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C
  • 16
  • [ 86232-28-2 ]
  • [ 86232-39-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C
Multi-step reaction with 5 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C
Multi-step reaction with 4 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating
Multi-step reaction with 4 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating

  • 17
  • [ 86232-28-2 ]
  • [ 86232-52-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 95 percent / 20 h / Heating
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 95 percent / 20 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 95 percent / 20 h / Heating
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 95 percent / 20 h / Heating

  • 18
  • [ 86232-28-2 ]
  • [ 86232-43-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating
Multi-step reaction with 5 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating
Multi-step reaction with 5 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating

  • 19
  • [ 86232-28-2 ]
  • [ 86232-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 6: 74 percent / NH2OH / methanol / 6 h / Heating
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 7: 74 percent / NH2OH / methanol / 6 h / Heating
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 6: 74 percent / NH2OH / methanol / 6 h / Heating
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 71 percent / conc. H2SO4 / 1,2-dichloro-ethane / 15 h / Heating 6: 74 percent / NH2OH / methanol / 6 h / Heating

  • 20
  • [ 86232-28-2 ]
  • [ 86232-50-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 7: 85 percent / Heating
Multi-step reaction with 8 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 8: 85 percent / Heating
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 7: 85 percent / Heating
Multi-step reaction with 7 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 91 percent / conc. H2SO4 / 1,2-dichloro-ethane 7: 85 percent / Heating

  • 21
  • [ 86232-28-2 ]
  • [ 86232-51-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / KMnO4 / H2O / 5 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 10 h / 20 °C 4: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 81 percent / 10percent aq. NaOH / 0.33 h
Multi-step reaction with 7 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 58 percent / KMnO4 / H2O / 10 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 10 h / 20 °C 5: 45 percent / silver oxide / dioxane; H2O / 1 h / 95 °C 6: 88 percent / AlBr3 / benzene / 3 h / Heating 7: 81 percent / 10percent aq. NaOH / 0.33 h
Multi-step reaction with 6 steps 1: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 2) reflux 2: 70 percent / N-bromosuccinimide, azoisobutyronitrile / CCl4 / 1 h / Heating; Irradiation 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 81 percent / 10percent aq. NaOH / 0.33 h
Multi-step reaction with 6 steps 1: 81 percent / NaBH4 / propan-2-ol / 1 h / Heating 2: 72 percent / SOCl2 / diethyl ether / 2 h / Heating 3: 95 percent / various solvent(s) / 2 h / 100 °C 4: 71 percent / KOH / aq. ethanol / 10 h / Heating 5: 88 percent / AlBr3 / benzene / 3 h / Heating 6: 81 percent / 10percent aq. NaOH / 0.33 h

  • 22
  • [ 148-53-8 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 45 percent / chlorine / acetic acid / 5 h / 20 °C 2: 1) 99percent hydrazine hydrate, 2) KOH / 1) reflux, 5 h, 2) reflux, 5 h 3: 75 percent / K2CO3 / acetone / 5 h / Heating
  • 23
  • [ 86232-28-2 ]
  • [ 117052-19-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) Mg / 2.) ether, benzene, reflux, 6 h 2: 85 percent / CrO3, pyridine / CH2Cl2 / 0.25 h
  • 24
  • [ 86232-28-2 ]
  • [ 117052-23-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) Mg / 2.) ether, benzene, reflux, 6 h 2: 85 percent / CrO3, pyridine / CH2Cl2 / 0.25 h 3: 65 percent / aq. conc. HCl / ethanol / 10 h / Heating
  • 25
  • [ 86232-28-2 ]
  • [ 75-16-1 ]
  • [ 117052-18-3 ]
YieldReaction ConditionsOperation in experiment
100% In diethyl ether at 20℃; for 4h; Reflux; 5 Example 5; The synthesis of ketone 3 was carried out by reducting the commercially available aldehyde 1 to the corresponding alcohol 2 following the procedure disclosed in WO06/081332A1, followed by the oxidation to ketone 3 with MnO2 with a good yield (Scheme 8).
96% Stage #1: 5-chloro-2,3-dimethoxybenzaldehyde; methylmagnesium bromide In diethyl ether; tert-butyl methyl ether at 9 - 33℃; Stage #2: With water; ammonium chloride In diethyl ether; tert-butyl methyl ether at 11 - 28℃; for 0.0833333h; 54 1 -(5 -Chloro-2,3 -dimethoxy-phenyl)-ethanol :; To a mixture of 5-chloro-2,3-dimethoxybenzaldehyde (339, 1.69 mol) in TBME (5.6 L) was added 3M methylmagnesium bromide in ether (660 mL, 1.98 mol) over 1 hour at 9 to 12 0C. The mixture was warmed at 33 0C for 1 hour 20 minutes. There was significant starting material present so more methylmagnesium bromide was added (590 mL, 1.77 mol) over 1 hour 20 minutes with the reaction temperature at 33 0C. The reaction was cooled to room temperature overnight and poured into ammonium chloride (20 wt %, 3 kg) over 5 minutes. The temperature rose from 11 to 28 0C. The reaction flask was rinsed with ammonium chloride solution (500 mL) and TBME (250 mL). The layers were separated and the organic layer was concentrated to an orange yellow thick oil. Yield: 348 g (96 % yield, 94 % purity).
75% Stage #1: 5-chloro-2,3-dimethoxybenzaldehyde; methylmagnesium bromide In diethyl ether at 0℃; for 3.5h; Heating / reflux; Stage #2: With water; ammonium chloride In diethyl ether at 0℃; 25 l-(5-Chloro-2,3-dimethoxy-phenyl)-ethanol:; To a stirred solution of 5-chloro-2,3-dimethoxy-benzaldehyde (7.Og, 34.90 mmol) in dry diethyl ether (500 mL) at 0 °C was added methylmagnesium bromide of 3.0 M in diethyl ether (29 mL, 87.22 mmol). The reaction mixture was brought to room temperature and stirred for 30 min; refluxed for 3 h; then cooled to 0 0C and quenched by adding saturated aqueous NH4Cl. The two liquid layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried, and concentrated to the crude compound which was purified by silica gel column (10-25 % ethyl acetate in hexanes) to afford l-(5-chloro-2,3-dimethoxy-phenyl)-ethanol (5.67 g, 75 %): 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1 H), 6.81 (d, 1 H), 5.11 (m, 1 H), 3.86 (s, 6 H), 2.30 (d, 1 H), 1.48 (d, 3 H). EPO
  • 26
  • [ 77-78-1 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 5-chloro-2-hydroxy-3-methoxy-benzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 22 - 29℃; for 0.25h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 28 - 61℃; for 2h; 54 5-Chloro-2,3-dimethoxybenzaldehyde:; A mixture of 5-Chloro-2-hydroxy-3-methoxybenzaldehyde (275 g, 1.47 mol) and DMF were stirred as potassium carbonate (411 g, 2.97 mol) was added over 5 minutes. The mixture temperature rose from 22 to 29 0C over 10 minutes. Dimethylsulfate (283 g, 2.24 mol) was EPO added over 15 minutes causing a temperature rise from 28 to 47 0C. The mixture was then heated with a heating mantle to 61 0C over 15 minutes and stirred at 61 0C for 1.5 hours; the reaction was complete by TLC. The reaction mixture was cooled to 22 0C, transferred to a 22-L flask and diluted with water (8.2 L) over 5 minutes; the temperature rose to 38 0C. The light yellow mixture was filtered and the flask and filter cake rinsed with 1.5 L water. The solid was dried under vacuum for 15 hour at 50 0C. The material contained inorganic salts and was suspended in water (3 L) for 1.5 hours. After filtration and a 500 mL water rinse, the filter cake was dried under by suction and overnight at 65 0C under vacuum. Yield: 305 g (100 % yield, 99.1 % purity).
  • 27
  • [ 86232-28-2 ]
  • [ 865-47-4 ]
  • [ 623-70-1 ]
  • [ 116314-08-0 ]
YieldReaction ConditionsOperation in experiment
7.3 g (55%) In 1-methyl-pyrrolidin-2-one 32 5-(3,4-Dimethoxy-5-chlorophenyl)-2,4-pentadienoic acid EXAMPLE 32 5-(3,4-Dimethoxy-5-chlorophenyl)-2,4-pentadienoic acid To a solution containing 10.0 g of dimethoxy-5-chlorobenzaldehyde and 8.3 ml of ethyl crotonate in 65 ml of N-methylpyrrolidone 6.7 g of potassium tert.-butoxide was added with stirring. The solution was stirred for 0.5 h more at 20° C. and the solution was poured then to a mixture of ice and hydrochloric acid and extracted with ether. The ether extract was washed with water and extracted then with NaHCO3 -solution. The aqueous phase was acidified with hydrochloric acid and the semisolid product was separated and washed with water. Yield 7.3 g (55%).
  • 28
  • [ 86232-28-2 ]
  • [ 439291-60-8 ]
  • [ 1189527-93-2 ]
YieldReaction ConditionsOperation in experiment
In toluene for 5.5h; Molecular sieve; Reflux; 1 N-[1-(5-Chloro-2,3-dimethoxyphenyl)ethyl]-N-[5-fluoro-2-(methylthio)phenyl]amine (6); [Show Image] To a solution of the amine (10.0 g, 63.61 mmol) in toluene (140 mL) was added the aldehyde (17.86 g, 89.05 mmol) and 4 Å molecular sieves (32.0 g). After heating at reflux for 5.5 h using a Dean-Stark, the reaction mixture was cooled at -78 °C and MeLi (79.5 mL, 1.6 M solution in Et2O, 127.22 mmol) was added dropwise (30 min addition). The mixture was stirred at this temperature for 0.5 h, quenched with H2O (100 mL) and molecular sieves removed by filtration, washing with CH2Cl2 (2.0 L). Layers were separated and the aqueous layer was extracted with CH2Cl2 (2x75 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was flash chromatographed on silica gel (3% AcOEt/Hexanes) to give 19.43 g of the title product (Rf= 0.7 (10% AcOEt/Hexanes), pale yellow solid, 86% yield). 1H-NMR (CDCl3, 250 MHz, δ): 7.36 (dd, J = 8.2, 6.6 Hz, 1H, ArH); 6.84 (d, J = 2.5 Hz, 1H, ArH); 6.78 (d, J = 2.5 Hz, 1H, ArH); 6.28 (td, J = 8.5, 2.7 Hz, 1H, ArH); 6.08 (dd, J = 11.7, 2.7 Hz, 1H, ArH); 5.52 (d, J = 5.2 Hz, 1H, NH); 4.79 (q, J = 6.6 Hz, 1H, CH); 3.93 (s, 3H, OCH3); 3.86 (s, 3H, OCH3); 2.32 (s, 3H, SCH3); 1.53 (d, J = 6.6 Hz, 3H, CH3). MS-ES+ m/z: 356.2 (M+1).
  • 29
  • [ 86232-28-2 ]
  • [ 139192-88-4 ]
  • [ 1189527-90-9 ]
YieldReaction ConditionsOperation in experiment
In toluene for 6h; Molecular sieve; Reflux; 4 N-[5-Bromo-2-(methylthio)phenyl]-N-[1-(5-chloro-2,3-dimethoxyphenyl)ethyl]amine (22); [Show Image] To a solution of starting amine (0.213 g, 0.98 mmol) in toluene (5.0 mL) was added aldehyde (0.255 g, 1.27 mmol) and 4 Å molecular sieves (2.00 g). After heating at reflux for 6 h using a Dean-Stark, the reaction mixture was cooled at -78 °C and MeLi (1.2 mL, 1.6 M solution in Et2O, 1.92 mmol) added dropwise. The mixture was stirred at this temperature for 0.5 h, quenched with H2O (10 mL) and molecular sieves were removed by filtration. The mother liquors were extracted with AcOEt (3x10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was flash chromatographed on silica gel (4% AcOEt/Hexanes) to give 0.330 g of the title product (Rf= 0.7 (10% AcOEt/Hexanes), pale yellow solid, 81% yield). 1P-NMR (CDCl3, 250 MHz, δ): 7.22 (d, J = 8.0 Hz, 1H, ArH); 6.84 (d, J = 2.2 Hz, 1H, ArH); 6.78 (d, J = 2.2 Hz, 1H, ArH); 6.72 (dd, J = 8.0, 2.0 Hz, 1H, ArH); 6.52 (d, J = 2.0 Hz, 1H, ArH); 5.35 (d, J = 6.5 Hz, 1H, NH); 4.82 (q, J = 6.5 Hz, 1H, CH); 3.95 (s, 3H, OCH3); 3.87 (s, 3H, OCH3); 2.34 (s, 3H, SCH3); 1.51 (d, J = 6.5 Hz, 3H, CH3).
  • 30
  • [ 1187659-03-5 ]
  • [ 86232-28-2 ]
  • [ 1189527-91-0 ]
YieldReaction ConditionsOperation in experiment
In toluene for 22h; Molecular sieve; Reflux; 2.2 The experimental procedure for Entry 2 is described below: [Show Image] To a solution of starting amine (1.602 g, 4.50 mmol) in toluene (60 mL) was added a solution of aldehyde (0.904 g, 4.50 mmol) in toluene (50 mL) and 4 Å molecular sieves (3.00 g). After heating at reflux for 6 h using a Dean-Stark, another portion of the aldehyde (0.093 g, 0.45 mmol) was added and the mixture stirred at the same temperature for another 16 h. Then, it was quickly concentrated, THF (110 mL) was added and the mixture was cooled at -78 °C. MeLi (8.4 mL, 1.6 M solution in Et2O, 13.50 mmol) was added dropwise (5 min addition) and the mixture stirred at this temperature for 2 h. The crude mixture was quenched with NH4Cl saturated aqueous solution (50 mL). Molecular sieves were filtered, mother liquors were extracted with AcOEt (4x100 mL) and the combined organic layers dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by medium flash chromatographed (Biotage system SP1, 15%→50% AcOEt/Hexanes) to give 0.863 g of the title product (Rf= 0.3 (2% MeOH/ CH2Cl2), white solid, 35% yield). 1H-NMR (CDCl3, 250 MHz, δ): 7.56 (s, 1H, ArH); 6.86 (d, J = 2.3 Hz, 1H, ArH); 6.76 (d, J = 2.3 Hz, 1H, ArH); 6.54 (d, J = 6.0 Hz, 1H, NH); 6.24 (dd, J = 8.9, 1.9 Hz, 1H, ArH); 5.97 (d, J = 1.9 Hz, 1H, ArH); 4.85 (q, J = 6.0 Hz, 1H, CH); 3.89 (s, 3H, OCH3); 3.85 (s, 3H, OCH3); 3.47 (m, 4H, CH2); 3.18 (m, 4H, CH2); 3.04 (s, 3H, SO2CH3); 1.54 (d, J = 6.0 Hz, 3H, CH3); 1.47 (s, 9H, Boc). MS-ES+ m/z: 554.8 (M+1).
  • 31
  • [ 86232-28-2 ]
  • [ 141-97-9 ]
  • [ 126-81-8 ]
  • [ 1372721-92-0 ]
YieldReaction ConditionsOperation in experiment
83% With ammonium acetate at 75℃; for 3h; Neat (no solvent);
  • 32
  • [ 495-69-2 ]
  • [ 86232-28-2 ]
  • [ 1444008-97-2 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: Hippuric Acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 5-chloro-2,3-dimethoxybenzaldehyde In tetrahydrofuran at 75℃; for 0.266667h;
  • 33
  • [ 7740-05-8 ]
  • [ 616-38-6 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
With tetrabutylammomium bromide; potassium carbonate at 110℃; for 12h; 2.2.4; 2.2.7 2.4 Preparation of 2,3-Dimethoxy-5-chlorobenzaldehyde Add 2-hydroxy-3-methoxy-5-chlorobenzaldehyde (2.3g, 12.3mmol), 17.5mL of dimethyl carbonate, tetrabutylammonium bromide (1.88g, 5.83mmol) and Potassium carbonate (3.41 g, 24.6 mmol) was uniformly dispersed at room temperature, and then the temperature was raised to 110° C. to react for 12 hours, and the reaction was monitored by TLC.Add appropriate amount of water to the reaction system, extract 3 times with ether in a separatory funnel, combine the organic phases, wash the organic phases with water and saturated brine respectively, dry with anhydrous Na2SO4and spin dry to obtain Brown solid crude 2,3-dimethoxy-5-chlorobenzaldehyde (2.3g, 95%, mp=80-84°C), content 96% (HPLC).
With tetrabutylammomium bromide; potassium carbonate at 20 - 110℃; for 12h; 8 Example 8 Preparation of 2,3-dimethoxy-5-chlorobenzaldehyde 2-Hydroxy-3-methoxy-5-chlorobenzaldehyde (2.3g, 12.3mmol), 17.5mL dimethyl carbonate,Tetrabutylammonium bromide (1.88g, 5.83mmol) and potassium carbonate (3.41g, 24.6mmol) were uniformly dispersed at room temperature,Then the temperature was raised to 110° C. for 12 hours, and the reaction was monitored by TLC.An appropriate amount of water was added to the reaction system, extracted three times with ether in a separating funnel, and the organic phases were combined.The organic phase was washed once with water and saturated brine, dried over anhydrous Na2SO4, and then spin-dried.The crude 2,3-dimethoxy-5-chlorobenzaldehyde was obtained as a brown solid (2.3 g, 95%, mp=80-84°C) with a content of 96% (HPLC).
  • 34
  • [ 16766-30-6 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydroxide; aluminum oxide / water / 0.08 h / Cooling with ice 1.2: 6 h / 60 °C / pH 9 - 10 2.1: iron(III) chloride / water; toluene / 4 h / 90 °C 3.1: tetrabutylammomium bromide; potassium carbonate / 12 h / 110 °C
Multi-step reaction with 3 steps 1.1: sodium hydroxide; aluminum oxide / water / 0.08 h / Cooling with ice 1.2: 6 h / 60 °C / pH 9 - 10 2.1: iron(III) chloride / water; toluene / 4 h / 90 °C 3.1: tetrabutylammomium bromide; potassium carbonate / 12 h / 20 - 110 °C
  • 35
  • [ 90-05-1 ]
  • [ 86232-28-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sulfuryl dichloride / chloroform / 24 h / -5 - 60 °C / Inert atmosphere 2.1: sodium hydroxide; aluminum oxide / water / 0.08 h / Cooling with ice 2.2: 6 h / 60 °C / pH 9 - 10 3.1: iron(III) chloride / water; toluene / 4 h / 90 °C 4.1: tetrabutylammomium bromide; potassium carbonate / 12 h / 110 °C
Multi-step reaction with 4 steps 1.1: sulfuryl dichloride / 24 h / -5 - 60 °C / Inert atmosphere 2.1: sodium hydroxide; aluminum oxide / water / 0.08 h / Cooling with ice 2.2: 6 h / 60 °C / pH 9 - 10 3.1: iron(III) chloride / water; toluene / 4 h / 90 °C 4.1: tetrabutylammomium bromide; potassium carbonate / 12 h / 20 - 110 °C
  • 36
  • [ 86232-28-2 ]
  • [ 1484-85-1 ]
  • 2-(3,4-methylenedioxyphenyl)-N-(5-chloro-2,3-dimethoxybenzyl)ethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 16 h / 20 °C / Molecular sieve; Inert atmosphere 2: sodium tetrahydroborate; methanol / dichloromethane / 0.67 h / 0 °C / Inert atmosphere
  • 37
  • [ 86232-28-2 ]
  • [ 1484-85-1 ]
  • C18H18ClNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.6 g In dichloromethane at 20℃; for 16h; Molecular sieve; Inert atmosphere; 16 Example 16 Preparation of 2-(3,4-methylenedioxyphenyl)-N-(5-chloro-2,3-dimethoxybenzyl)ethanamine Under the protection of argon, 8.6g 4A molecular sieves were placed in the reactor, the reaction system was baked 3 times, followed by 80mL dichloromethane solution of methylenedioxyphenethylamine (2.8g, 17.4mmol) and 5-bromo-o-veratrol. A solution of aldehyde (3.5 g, 17.4 mmol) in 80 mL of dichloromethane was injected into the above reaction system and mixed evenly. The reaction solution was brownish-yellow and turbid. The reaction was carried out at room temperature for 16 hours, and the reaction was detected by TLC dot plate. The 4A molecular sieves were removed by diatomaceous earth filtration, the filter cake was washed with a small amount of dichloromethane, the filtrate was collected and the solvent was removed under reduced pressure to obtain 7.6 g of the imine intermediate. Under argon, the crude imine intermediate was redissolved with methanol-dichloromethane (75 mL, v:v=1:1),Afterwards, the reaction system was moved to 0°C and pre-cooled for 10 minutes. Sodium borohydride (1.25 g, 33 mmol) was added to it in batches, and The reaction solution changed from brownish yellow to light yellow and clear, and the reaction was continued to be stirred at 0° C. for 30 min, and the reaction was monitored by TLC dot plate. To the reaction system, add Sat.NH Cl solution to quench the reaction, then remove excess methanol and dichloromethane solvent under reduced pressure,The residue was redissolved with ether, extracted with water/ether for 3 times, the organic phases were combined, and the organic phases were backwashed once with saturated brine,Dry over anhydrous sodium sulfate and spin to dry to obtain a yellow oily product of 2-(3,4-dioxyphenyl)-N-(5-chloro-2,3-dimethoxybenzyl)ethanamine crude product (5.9 g, 98%).
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