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Product Details of [ 15393-58-5 ]

CAS No. :15393-58-5 MDL No. :MFCD11554963
Formula : C10H11ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :NLTONRXIPNPAGV-UHFFFAOYSA-N
M.W : 198.65 Pubchem ID :9813057
Synonyms :

Safety of [ 15393-58-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15393-58-5 ]

* 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 [ 15393-58-5 ]

[ 15393-58-5 ] Synthesis Path-Downstream   1~46

  • 1
  • [ 109-95-5 ]
  • 4-chloro-2-methylbenzamide [ No CAS ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
at 140℃; im Druckrohr;
  • 2
  • [ 64-17-5 ]
  • [ 7499-07-2 ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
  • 3
  • [ 15393-58-5 ]
  • [ 15365-28-3 ]
YieldReaction ConditionsOperation in experiment
98.9% With dihydrogen peroxide; bromine In dichloromethane; lithium hydroxide monohydrate at 20℃; for 24h; 5 Compound 5b (1.99 g, 10 mmol)Dissolve in dichloromethane (25 mL), add water (25 mL), and stir at room temperature.Bromine (520 μL, 10 mmol) and 30% hydrogen peroxide (1 mL) were added dropwise in sequence,Continue stirring and react for 24 hours.25 mL of dichloromethane was added, shaken evenly, and the organic layer was separated; the aqueous layer was extracted with dichloromethane (25 mL×2). The organic phases were combined, washed with saturated brine (50 mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a yellow liquid. Purified by silica gel column chromatography (petroleum ether/ethyl acetate (V/V)=40/1). 2.75 g of colorless liquid compound 5c was obtained, yield: 98.9%.
98.9% With dihydrogen peroxide; bromine In dichloromethane; lithium hydroxide monohydrate at 20℃; for 24h; 5 Compound 5b (1.99 g, 10 mmol) was dissolved in dichloromethane (25 mL), water (25 mL) was added, and the mixture was stirred at room temperature. Bromine (520 μL, 10 mmol) and 30% hydrogen peroxide (1 mL) were successively added dropwise, and the reaction was continued for 24 hours. 25 mL of dichloromethane was added, shaken evenly, and the organic layer was separated; the aqueous layer was extracted with dichloromethane (25 mL×2). The organic phases were combined, washed with saturated brine (50 mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a yellow liquid. Purified by silica gel column chromatography (petroleum ether/ethyl acetate (V/V)=40/1). 2.75 g of colorless liquid compound 5c was obtained, yield: 98.9%.
98.9% With dihydrogen peroxide; bromine In dichloromethane; lithium hydroxide monohydrate at 20℃; for 24h; Compound 5b (1.99 g, 10 mmol) was dissolved in dichloromethane (25 mL), water (25 mL) was added, and the mixture was stirred at room temperature. Bromine (520 μL, 10 mmol) and 30% hydrogen peroxide (1 mL) were successively added dropwise, and the reaction was continued for 24 hours. 25 mL of dichloromethane was added, shaken evenly, and the organic layer was separated; the aqueous layer was extracted with dichloromethane (25 mL×2). The organic phases were combined, washed with saturated brine (50 mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a yellow liquid. Purified by silica gel column chromatography (petroleum ether/ethyl acetate (V/V)=40/1). 2.75 g of colorless liquid compound 5c was obtained, yield: 98.9%.
55% With NBS; azobisisobutyronitrile In Carbon tetrachloride for 3h; Reflux;
With NBS
With NBS; azobisisobutyronitrile In Carbon tetrachloride for 3.5h; Reflux;
With NBS 10.a EXAMPLE 10 a. Reaction of ethyl 4-chloro-o-toluate with N-bromosuccinimide as described in Example 1a provides ethyl α-bromo-4-chloro-o-toluate as an oil.

  • 4
  • [ 15393-58-5 ]
  • [ 16470-09-0 ]
YieldReaction ConditionsOperation in experiment
(i) LiAlH4, THF, (ii) SOCl2; Multistep reaction;
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran 2: pyridine; thionyl chloride / dichloromethane
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Heating / reflux 2: thionyl chloride / 1 h
  • 5
  • [ 15393-58-5 ]
  • [ 129716-11-6 ]
YieldReaction ConditionsOperation in experiment
97% With lithium aluminium tetrahydride In tetrahydrofuran 11 A sample of 4-chloro-2-methylbenzoic acid was converted to the ethyl ester using ethanol/triethyl orthoformate/sulfuric acid in >95% yield. Reduction of the ester with LiAlH4/tetrahydrofuran gave 4-chloro-2-methylbenzyl alcohol in 97% yield as a colorless oil. Subsequent treatment with thionyl chloride/pyridine/CH2Cl2 gave the substituted benzyl chloride. The latter, on treatment with 40% excess sodium cyanide in DMF at 90° C. for 20 min. and normal work-up and crystallization from hexane/butyl chloride (2 crops) gave 4-chloro-2-methylbenzyl cyanide in 80% overall yield.This latter compound on treatment with formaldehyde in the presence of DBU was found to quickly form an equilibrium at relatively low conversion to the desired alcohol which was then slowly dehydrated to an atroponitrile. Consequently, a mixture of the nitrile (688 mg, 4.15 mmol) and formaldehyde in THF (2.75 mL) was treated with DBU (55 μL), then quenched at 7 min with 3N HCl. Work-up recovered starting material (528 mg) by crystallization from butyl chloride/hexane. Two cycles of retreatment followed by flash chromatography (5% 90% ethyl acetate in hexane) recovered 313 mg of the desired alcohol as a pale yellow oil. TLC: Rf 0.13 (silica gel, ethyl acetate:hexane=1:4)
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Reflux; The 4-chloro-2-methyl-benzyl chloride is readily synthesized according to the following scheme from T. S Osdene and et al, Journal of Medicinal Chemistry., 10, 431-434 (1967).
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating / reflux;

  • 6
  • [ 64-17-5 ]
  • [ 108-41-8 ]
  • [ 75-36-5 ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
(i) AlCl3, CS2, (ii) aq. NaOBr, (iii) /BRN= 1718733/, H2SO4; Multistep reaction;
YieldReaction ConditionsOperation in experiment
Rk. mit N-Brom-succinimid -> α-Brom-4-chlor-o-toluylsaeure-ethylester;
YieldReaction ConditionsOperation in experiment
3-Chlor-toluol, 1.) Acetylchlorid, AlCl3, Δ, 2.) Natriumhypobromit, Oxid., 3.) A., konz. H2SO4, Δ;
  • 10
  • [ 120-66-1 ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: glacial acetic acid; calcium chloride / 0 °C / Verseifung des entstandenen Acetylderivats mit alkoholischer Kalilauge 2: hydrochloric acid / Diazotization.Eintragen von Kaliumcuprocyanidloesung in Diazoniumsalzloesung 3: KOH-solution 4: HCl
Multi-step reaction with 4 steps 1: glacial acetic acid; calcium chloride / 0 °C / Verseifung des entstandenen Acetylderivats mit alkoholischer Kalilauge 2: hydrochloric acid / Diazotization.Eintragen von Kaliumcuprocyanidloesung in Diazoniumsalzloesung 3: KOH-solution 4: 140 °C / im Druckrohr
  • 11
  • [ 95-69-2 ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrochloric acid / Diazotization.Eintragen von Kaliumcuprocyanidloesung in Diazoniumsalzloesung 2: KOH-solution 3: HCl
Multi-step reaction with 3 steps 1: hydrochloric acid / Diazotization.Eintragen von Kaliumcuprocyanidloesung in Diazoniumsalzloesung 2: KOH-solution 3: 140 °C / im Druckrohr
  • 12
  • [ 15393-58-5 ]
  • [ 16470-10-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) LiAlH4, THF, (ii) SOCl2 2: ethanol; H2O
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran 2: pyridine; thionyl chloride / dichloromethane 3: N,N-dimethyl-formamide / 0.33 h / 90 °C
  • 13
  • [ 7499-07-2 ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
8.a a a Ethyl 4-chloro-2-methylbenzoate By using 4-chloro-2-methylbenzoic acid (300 mg, 1.76 mmol), the title compound was obtained as colorless solid by similar procedures to those of Example 3a (347 mg). The product was used in the next reaction without purification.
  • 14
  • [ 7499-07-2 ]
  • [ 122-51-0 ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
95% With ethanol 11 A sample of 4-chloro-2-methylbenzoic acid was converted to the ethyl ester using ethanol/triethyl orthoformate/sulfuric acid in >95% yield. Reduction of the ester with LiAlH4/tetrahydrofuran gave 4-chloro-2-methylbenzyl alcohol in 97% yield as a colorless oil. Subsequent treatment with thionyl chloride/pyridine/CH2Cl2 gave the substituted benzyl chloride. The latter, on treatment with 40% excess sodium cyanide in DMF at 90° C. for 20 min. and normal work-up and crystallization from hexane/butyl chloride (2 crops) gave 4-chloro-2-methylbenzyl cyanide in 80% overall yield.This latter compound on treatment with formaldehyde in the presence of DBU was found to quickly form an equilibrium at relatively low conversion to the desired alcohol which was then slowly dehydrated to an atroponitrile. Consequently, a mixture of the nitrile (688 mg, 4.15 mmol) and formaldehyde in THF (2.75 mL) was treated with DBU (55 μL), then quenched at 7 min with 3N HCl. Work-up recovered starting material (528 mg) by crystallization from butyl chloride/hexane. Two cycles of retreatment followed by flash chromatography (5% 90% ethyl acetate in hexane) recovered 313 mg of the desired alcohol as a pale yellow oil. TLC: Rf 0.13 (silica gel, ethyl acetate:hexane=1:4)
  • 15
  • [ 7499-07-2 ]
  • [ 75-03-6 ]
  • [ 15393-58-5 ]
YieldReaction ConditionsOperation in experiment
83.4% Stage #1: 4-chloro-2-methylbenzoic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: ethyl iodide In N,N-dimethyl-formamide 5 Compound 5a (3.42 g, 20 mmol)Dissolve in DMF (25 mL), add potassium carbonate (8.30 g, 60 mmol), and stir at room temperature for 30 min. Add iodoethane (2.4 mL, 30 mmol) dropwise, continue stirring,React overnight. 100 mL of ethyl acetate and 100 mL of water were added, shaken uniformly, and the organic layer was separated; the aqueous layer was extracted with ethyl acetate (50 mL×2). The organic phases were combined, washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a yellow liquid. Purified by silica gel column chromatography (petroleum ether/ethyl acetate (V/V)=40/1).3.32 g of colorless liquid compound 5b was obtained, yield: 83.4%.
83.4% Stage #1: 4-chloro-2-methylbenzoic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.75h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 20℃; 5 5. 8-Chloro-6,11-dihydrodibenzo[b,e]thiazepin-11-one (Compound 5) Compound 5a (3.42 g, 20 mmol) was dissolved in DMF (25 mL), potassium carbonate (8.30 g, 60 mmol) was added, and the mixture was stirred at room temperature for 30 min. Iodoethane (2.4 mL, 30 mmol) was added dropwise, stirring was continued, and the reaction was continued overnight. 100 mL of ethyl acetate and 100 mL of water were added, shaken uniformly, and the organic layer was separated; the aqueous layer was extracted with ethyl acetate (50 mL×2). The organic phases were combined, washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a yellow liquid. Purified by silica gel column chromatography (petroleum ether/ethyl acetate (V/V)=40/1). 3.32 g of colorless liquid compound 5b was obtained, yield: 83.4%.
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
  • 16
  • [ 15393-58-5 ]
  • C14H8Cl2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C
  • 17
  • [ 15393-58-5 ]
  • C14H8Cl2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C
  • 18
  • [ 15393-58-5 ]
  • 8-chloro-11-hydroxy-6,11-dihydrodibenz[b,e]oxepin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C
  • 19
  • [ 15393-58-5 ]
  • C14H10Cl2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C
  • 20
  • [ 15393-58-5 ]
  • C14H10Cl2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C
  • 21
  • [ 15393-58-5 ]
  • C19H21ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C 7: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C 8: chloroform / 2 h / 0 - 20 °C
  • 22
  • [ 15393-58-5 ]
  • C19H20Cl2N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C 7: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C 8: chloroform / 2 h / 0 - 20 °C
  • 23
  • [ 15393-58-5 ]
  • C19H20Cl2N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C 7: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C 8: chloroform / 2 h / 0 - 20 °C
  • 24
  • [ 15393-58-5 ]
  • C14H10Cl2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 3 h / 80 °C 3.1: sodium hydroxide / ethanol; water / 1 h / 100 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
  • 25
  • [ 15393-58-5 ]
  • C14H9Cl3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux
  • 26
  • [ 15393-58-5 ]
  • C14H9Cl3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux
  • 27
  • [ 15393-58-5 ]
  • 8,11-Dichloro-6,11-dihydrodibenz[b,e,]oxepin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C 7: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C
  • 28
  • [ 15393-58-5 ]
  • C14H9Cl3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C 7: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C
  • 29
  • [ 15393-58-5 ]
  • C14H9Cl3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 6: sodium tetrahydroborate / methanol / 2 h / 20 °C 7: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C
  • 30
  • [ 15393-58-5 ]
  • ethyl 4-chloro-2-(phenoxymethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 3 h / 80 °C
  • 31
  • [ 15393-58-5 ]
  • C16H14Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux
  • 32
  • [ 15393-58-5 ]
  • C16H14Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux
  • 33
  • [ 15393-58-5 ]
  • C16H14Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux
  • 34
  • [ 15393-58-5 ]
  • [ 515133-99-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 3 h / 80 °C 3.1: sodium hydroxide / ethanol; water / 1 h / 100 °C
  • 35
  • [ 15393-58-5 ]
  • C14H10Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux
  • 36
  • [ 15393-58-5 ]
  • C14H10Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux
  • 37
  • [ 15393-58-5 ]
  • C14H10Cl2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux
  • 38
  • [ 15393-58-5 ]
  • [ 515134-00-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3.5 h / Reflux 2: sodium ethanolate / ethanol / 6.5 h / Reflux 3: sodium hydroxide; water / ethanol / 1 h / Reflux 4: thionyl chloride / 1 h / Reflux 5: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 3 h / 80 °C 3.1: sodium hydroxide / ethanol; water / 1 h / 100 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 5.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C
  • 39
  • [ 15393-58-5 ]
  • ethyl 4-(2-ethoxycarbonyl-5-chlorobenzyloxy)phenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide
  • 40
  • [ 15393-58-5 ]
  • [ 55689-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide 3: potassium hydroxide
  • 41
  • [ 15393-58-5 ]
  • [ 55690-25-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide 3: potassium hydroxide
  • 42
  • [ 15393-58-5 ]
  • [ 1034694-63-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran 2: pyridine; thionyl chloride / dichloromethane 3: N,N-dimethyl-formamide / 0.33 h / 90 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran
  • 43
  • [ 15393-58-5 ]
  • (E)-3-(8-chlorodibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine [ No CAS ]
  • (Z)-3-(8-chlorodibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 3 h / 80 °C 3.1: sodium hydroxide / ethanol; water / 1 h / 100 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 5.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C 6.1: iodine; magnesium / tetrahydrofuran / Reflux 6.2: 2 h / 65 °C / Inert atmosphere 6.3: 1 h / Inert atmosphere
  • 44
  • [ 15393-58-5 ]
  • C16H15ClO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bromine; dihydrogen peroxide / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 2 steps 1: dihydrogen peroxide; bromine / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C
  • 45
  • [ 15393-58-5 ]
  • [ 54109-04-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bromine; dihydrogen peroxide / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C
Multi-step reaction with 3 steps 1: bromine; dihydrogen peroxide / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: lithium hydroxide monohydrate; sodium hydroxide / methanol; tetrahydrofuran / 4 h / 20 °C
Multi-step reaction with 3 steps 1: dihydrogen peroxide; bromine / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: sodium hydroxide / lithium hydroxide monohydrate; methanol; tetrahydrofuran / 4 h / 20 °C
  • 46
  • [ 15393-58-5 ]
  • [ 30250-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: bromine; dihydrogen peroxide / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C 4: polyphosphoric acid / 4 h / 120 °C
Multi-step reaction with 4 steps 1: bromine; dihydrogen peroxide / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: lithium hydroxide monohydrate; sodium hydroxide / methanol; tetrahydrofuran / 4 h / 20 °C 4: polyphosphoric acid / 4 h / 120 °C
Multi-step reaction with 4 steps 1: dihydrogen peroxide; bromine / dichloromethane; lithium hydroxide monohydrate / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: sodium hydroxide / lithium hydroxide monohydrate; methanol; tetrahydrofuran / 4 h / 20 °C 4: polyphosphoric acid / 4 h / 120 °C
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