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Chemical Structure| 3321-92-4 Chemical Structure| 3321-92-4

Structure of 3321-92-4

Chemical Structure| 3321-92-4

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Product Details of [ 3321-92-4 ]

CAS No. :3321-92-4
Formula : C8H6Cl2O2
M.W : 205.04
SMILES Code : CC(C1=CC(Cl)=CC(Cl)=C1O)=O
MDL No. :MFCD00016417
InChI Key :CJFYGRLJDKWMDI-UHFFFAOYSA-N
Pubchem ID :520608

Safety of [ 3321-92-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 3321-92-4 ]

* 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 [ 3321-92-4 ]

[ 3321-92-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 6341-97-5 ]
  • [ 3321-92-4 ]
YieldReaction ConditionsOperation in experiment
aluminium chloride; EXAMPLE 11 2-(5-chloro-2-hydroxybenzyl)-6-[1-(3,5-dichloro-2-hydroxyphenyl)ethyl]-4-fluorophenol (36) Powdered anhydrous aluminium chloride (100 g) was added to 2,4-dichloro-phenyl acetate at room temperature with stirring. The temperature was increased to 150-160 for 40 min. Treatment of the reaction mixture with ice-water and hydrochloric acid gave 3,5-dichloro-2-hydroxy-acetophenone (63 g, m.p. 99).
  • 3
  • [ 3321-92-4 ]
  • [ 35504-02-0 ]
YieldReaction ConditionsOperation in experiment
With sodium borohydrid; In ethanol; 3,5-Dichloro-2-hydroxyacetophenone (40 g) was treated in ethanol with sodium borohydride (4 g). The solid reaction product was recrystallized from benzene to give 2,4-dichloro-6-(1'-hydroxy ethyl) phenol (32 g, m.p. 70).
  • 4
  • [ 3321-92-4 ]
  • [ 5392-12-1 ]
  • (E)-1-(3,5-Dichloro-2-hydroxy-phenyl)-3-(2-methoxy-naphthalen-1-yl)-propenone [ No CAS ]
  • 5
  • [ 3321-92-4 ]
  • [ 78224-94-9 ]
  • 6
  • [ 3321-92-4 ]
  • [ 66-77-3 ]
  • (E)-1-(3,5-dichloro-2-hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydroxide; In ethanol; water; at 20℃;pH 12.0; General procedure: A mixture of the acetophenone (5-10 mmol, 1 equiv.) and thecorresponding aldehyde (1 equiv.) in EtOH (20-40 mL) was stirred atroom temperature and a 50% aqueous solution of NaOH (5-8 mL) wasadded. The reaction mixture was stirred at room temperature until thestarting materials had been consumed. HCl (10%) was then added untilneutrality was reached. Precipitated chalcones were generally filteredand crystallized from MeOH although in some cases, the product waspurified using column chromatography.
  • 13
  • [ 3321-92-4 ]
  • [ 53244-91-0 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 40℃;Darkness; General procedure: Ketone (1 eq) and N-bromosuccinimide (NBS) (2 eq) were solved in acetonitrile and trimethylsilyl trifluoromethanesulfonate (TMS-OTf) (1 eq) was added. The reactions were stirred at T = 40 C until completeness, diluted with diethyl ether (2 ml), washed with H2O (3 x 2 ml), dried over Na2SO4 and concentrated under reduced pressure. This procedure provided bromoketones intermediates in 75-90% overall yield, with purities generally >90% as determined by HPLC-MS. The compounds was used without further purification.
With copper(ll) bromide; In ethyl acetate; for 10h;Reflux; General procedure: CuBr2 (450 mg, 2.0 mmol) was added to a solution of commercially available, substituted o-hydroxyacetophenone (1.0 mmol) in EtOAc (30 mL) at 25 C. The reaction mixture was stirred at reflux for 10 h. Then, the reaction mixture was cooled to 25 C, filtered, neutralized with saturated aq NaHCO3 (30 mL) and extracted with EtOAc (3 × 30 mL). The combined organic layers were washed with brine, dried, filtered and evaporated under reduced pressure to afford crude product. Without further purification, substituted sodium sulfinate (2.1 mmol) was added to the resulting substituted α-bromo-o-hydroxyacetophenone in a cosolvent of dioxane and water [20 mL, 1:1 (v/v)] at 25 C. The reaction mixture was stirred at reflux for 3 h. Then, the reaction mixture was cooled to 25 C and extracted with CH2Cl2 (3 × 30 mL). The combined organic layers were washed with brine, dried, filtered and evaporated under reduced pressure to afford crude product. Purification on silica gel (hexanes/EtOAc, 10:1-2:1) afforded skeleton 1, known compounds whose analytical data are consistent with the literature.12b
  • 14
  • [ 98-03-3 ]
  • [ 3321-92-4 ]
  • (E)-1-(3,5-Dichloro-2-hydroxy-phenyl)-3-thiophen-2-yl-propenone [ No CAS ]
  • 15
  • [ 3321-92-4 ]
  • [ 86-81-7 ]
  • (E)-1-(3,5-Dichloro-2-hydroxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propenone [ No CAS ]
  • 16
  • [ 3321-92-4 ]
  • [ 100-10-7 ]
  • (E)-1-(3,5-Dichloro-2-hydroxy-phenyl)-3-(4-dimethylamino-phenyl)-propenone [ No CAS ]
  • 17
  • [ 3321-92-4 ]
  • [ 589-21-9 ]
  • 3,5-dichloro-2-hydroxyacetophenone 4-bromophenylhydrazone [ No CAS ]
  • 18
  • [ 3321-92-4 ]
  • [ 139755-99-0 ]
  • [ 778639-43-3 ]
  • 19
  • [ 3321-92-4 ]
  • [ 139756-00-6 ]
  • [ 778639-50-2 ]
  • 20
  • [ 3321-92-4 ]
  • [ 33513-42-7 ]
  • [ 64481-10-3 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate; at 0 - 64℃; for 4h; General procedure: To a cooled (0C)solution of 2'-hydroxyacetophenone (1 g, 1 eq) in DMF (30 mL) was added phosphorusoxychloride (5 eq). The mixture stirred at 64 C for 4 h until the 2'-hydroxyacetophenone consumed completely (TLC). The reaction was quenched withglacial water (100 mL), and the mixture stirred for an additional 30 mins. Then themixture was extracted three times with dichloromethane (100 mL). And then the solventwas evaporated in vacuo and the crude product was purified by column chromatographyon silica gel.
  • 21
  • [ 3321-92-4 ]
  • [ 210825-11-9 ]
  • 1-(3,5-dichloro-2-hydroxy-phenyl)-3-(1-phenyl-3-thiophen-2-yl-1<i>H</i>-pyrazol-4-yl)-propenone [ No CAS ]
  • 22
  • [ 3321-92-4 ]
  • [ 86-81-7 ]
  • 3',5'-dichloro-2'-hydroxy-3,4,5-trimethoxychalcone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In ethanol; water; at 50 - 60℃; Example 1; Synthesis of Chalcones 5-10; Employing the general method described by N. N. Mateeva et al, J. Heterocyclic Chem., 39, 1251 (2002); D. K. Bhardwaj et al, Indian J. Chem., 27B, 261 (1988) and K. Krohn et al, Phytochemistry 61.931 (2002), The corresponding substituted acetophenones 1 were mixed with an equimolar amount of 3,4-dimethoxybenzaldehyde or 3,4,5-trimethoxybenzaldehyde, 2, in ethanol (Scheme 1). 5 Milliliters of 50% aqueous KOH was added and the reaction mixture heated at 50-60 C. for 2-6 h. The product precipitated after cooling as yellow crystals, which were collected, recrystallized from CH3OH/CH2Cl2 and finally purified by column chromatography, using CH2Cl2:hexane 5:1 as eluent. The yields were 60-80%.
With potassium hydroxide; In ethanol; at 50 - 60℃; EXAMPLE 1 Synthesis of Chalcones 5-10 Employing the general method described by N. N. Mateeva et al, J. Heterocyclic Chem., 39, 1251 (2002); D. K. Bhardwaj et al, Indian J. Chem., 27B, 261 (1988) and K. Krohn et al, Phytochemistry 6 1.93 1 (2002), the corresponding substituted acetophenones 1 were mixed with an equimolar amount of 3,4-dimethoxybenzaldehyde or 3,4,5-trimethoxybenzaldehyde, 2, in ethanol (Scheme 3). 5 Milliliters of 50% aqueous KOH was added and the reaction mixture heated at 50-60 C. for 2-6 h. The product precipitated after cooling as yellow crystals, which were collected, recrystallized from CH3OH/CH2Cl2 and finally purified by column chromatography, using CH2Cl2:hexane 5:1 as eluent. The yields were 60-80%.
  • 25
  • [ 3321-92-4 ]
  • [ 123-11-5 ]
  • [ 62069-84-5 ]
YieldReaction ConditionsOperation in experiment
57% With sodium hydroxide; In methanol; Preparation 1 Synthesis of 1-(3,5-Dichloro-2-hydroxy-phenyl)-3-(4-methoxy-phenyl)-propenone 1.0 g (4.8 mmol) of <strong>[3321-92-4]3',5'-dichloro-2'-hydroxyacetophenone</strong> was dissolved in 30 ml of methanol solvent, and then 0.53 g of NaOH (13.2 mmol) was added thereto. The mixture was stirred for 30 minutes. 0.61 g (4.8 mmol) of 4-methoxybenzaldehyde was added thereto, the mixture was heated to 50 C., and then it was stirred for 3 hours. After the reaction was completed, methanol was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethylacetate=4/1, v/v) to give the title compound in a yield of 57%. 1H NMR (500 MHz, CDCl3): δ 8.52 (m, 1H), 7.60-7.02 (m, 5H), 6.22-6.00 (m, 2H), 3.90 (s, 3H); MS (FAB): 323 (M+H+).
  • 26
  • [ 118-93-4 ]
  • [ 3321-92-4 ]
YieldReaction ConditionsOperation in experiment
With chlorine; iron(III) chloride; In water; EXAMPLE 6 Preparation of 3',5'-dichloro-2'-hydroxyacetophenone Into a 500-milliliter four-neck, round-bottom flask, fitted with a condenser, mechanical stirrer, and thermometer were placed 150 millimeters of glacial acetic acid, 27.2 grams of 2'-hydroxyacetophenone, 100 milliliters of water, and 0.5 gram of ferric chloride. The resulting dark solution was chilled to 5 C., and 20 grams of chlorine was slowly introduced under the surface of the solution. The color of the solution became yellow as a heavy precipitate was formed. The cooling bath was removed, and stirring was continued at ambient temperature for an additional 1.5-2 hours. The mixture was poured into 500 milliters of water, filtered, and the solid precipitate was washed with water.
  • 27
  • [ 874672-97-6 ]
  • [ 3321-92-4 ]
  • 1-(3,5-dichloro-2-hydroxyphenyl)3-(4-(difluoromethoxy)dibenzofuran-1-yl)-prop-2-en-1-one [ No CAS ]
  • 28
  • [ 3321-92-4 ]
  • [ 4521-61-3 ]
  • 6,8-dichloro-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 2; Synthesis of Flavones 17-22; Employing the general method described by Mateeva, supra, T. Hone et al, Chem. Pharm. Bull., 43, 2054 (1995) and C. J. Bennett et al, Bioorganic & Medicinal Chemistry, 12, 2079 (2004). Compounds 3 (Scheme 2) were mixed with 1.7 times excess of 3,4,5-trimethoxy benzoyl chloride or 3,4-dimethoxy benzoyl chloride, 4, correspondingly, in pyridine. The reaction mixture was heated at 70 C. for 4 h, and then poured onto ice containing 5 N HCL. The precipitate that formed was collected by vacuum filtration and air dried. The crude product was dissolved in pyridine in the presence of 10 times excess of KOH.The reaction was carried out for 4 h at 65 DC, and then the mixture poured onto an iced 5 N HCl bath. A yellow precipitate was formed, which was collected by filtration and air dried. The crude product was dissolved in acetic acid containing 1 mL concentrated H2SO4, heated at 60 C. for 4 h and left stirring overnight at room temperature. After 24 h, the reaction mixture was poured onto an ice-NaHC03 mixture, the product collected by filtration and recrystallized from ethanol.The pure flavone was obtained by purification on Chromatotrone with CH2Cl2:MeOH 8:1 as eluent. The yields were 30-50%.
EXAMPLE 2 Synthesis of Flavones 17-22 Employing the general method described by Mateeva, supra, T. Hone et al, Chem. Pharm. Bull., 43,2054 (1995) and C. J. Bennett et al, Bioorganic & Medicinal Chemistry, 12,2079 (2004). Compounds 3 (Scheme 4) were mixed with 1.7 times excess of 3,4,5-trimethoxy benzoyl chloride or 3,4-dimethoxy benzoyl chloride, 4, correspondingly, in pyridine. The reaction mixture was heated at 70 C. for 4 h, and then poured onto ice containing 5 N HCL. The precipitate that formed was collected by vacuum filtration and air dried. The crude product was dissolved in pyridine in the presence of 10 times excess of KOH.The reaction was carried out for 4 h at 65 C., and then the mixture poured onto an iced 5N HCl bath. A yellow precipitate was formed, which was collected by filtration and air dried. The crude product was dissolved in acetic acid containing 1 mL concentrated H2SO4, heated at 60 C. for 4 h and left stirring overnight at room temperature. After 24 h, the reaction mixture was poured onto an ice-NaHCO3 mixture, the product collected by filtration and recrystallized from ethanol.The pure flavone was obtained by purification on Chromatotrone with CH2Cl2:MeOH 8:1 as eluent. The yields were 30-50%.
  • 30
  • [ 127406-56-8 ]
  • [ 3321-92-4 ]
  • C20H13Cl2NO2 [ No CAS ]
  • 31
  • [ 3321-92-4 ]
  • [ 1252045-63-8 ]
  • [ 1252045-66-1 ]
  • 32
  • [ 3321-92-4 ]
  • [ 36640-50-3 ]
  • [ 1246356-31-9 ]
  • 33
  • [ 3321-92-4 ]
  • [ 459-57-4 ]
  • [ 1224514-31-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In ethanol; at 0 - 20℃; General procedure: 2-Hydoxyacetophenones 1a-f (0.01 mol) and 4-fluorobenzaldehyde (0.01 mol) were added to a solution of KOH (0.03 mol) in ethanol (15 mL) at 0-5 C. The reaction mixture was stirred 2-3 h at room temperature. Then the reaction mixture was poured over crushed ice and neutralized carefully with 2 N HCl, and the obtained precipitate was filtered, washed with water, and dried. The crude product was crystallized with chloroform-ethanol to afford desired compound.
  • 34
  • [ 3321-92-4 ]
  • [ 1156334-11-0 ]
  • C22H13Cl3N2O2S [ No CAS ]
  • 35
  • [ 3321-92-4 ]
  • [ 1253514-17-8 ]
  • [ 1253513-45-9 ]
 

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• Acidity of Phenols • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Halogenation of Phenols • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reformatsky Reaction • Reimer-Tiemann Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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