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[ CAS No. 4023-81-8 ] {[proInfo.proName]}

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Product Details of [ 4023-81-8 ]

CAS No. :4023-81-8 MDL No. :MFCD04619579
Formula : C10H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GIKXMINIUUFRFD-UHFFFAOYSA-N
M.W : 241.08 Pubchem ID :432653
Synonyms :

Safety of [ 4023-81-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4023-81-8 ]

* 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 [ 4023-81-8 ]

[ 4023-81-8 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 4023-81-8 ]
  • [ 145353-53-3 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate; In methanol; for 2h;Reflux; Add a 100 ml round bottom flask to the magnet and add 1-p-bromophenylbutane-1,3-dione inward. (4.82g, 20mmol, 1.0eq) And hydrazine hydrate (1.1g, 20mmol, 1.0eq), then add methanol 50 ml, heated under reflux for 2 h, extracted with ethyl acetate Silica gel column chromatography to give 3-methyl-5-p-bromophenyl 1-hydropyrazole;
  • 2
  • [ 99-90-1 ]
  • [ 141-78-6 ]
  • [ 4023-81-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; at 20℃;Cooling with ice; Add a 100 ml round bottom flask to the magnetizer and add sodium hydride inward. (0.88 g, 22 mmol, purity 60%, 1.1 eq), then 50 ml of ethyl acetate was added under ice bath. Slowly adding p-bromoacetophenone (3.98g, 20mmol, 1.0eq), after 30min in ice bath, react at room temperature for more than 10h, TLC plate was monitored and the reaction was completed and quenched with 10% ammonium chloride. Extraction with ethyl acetate, spin-drying solvent, silica gel column chromatography to give 1-p-bromophenylbutane-1,3-dione.
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere; General procedure: In a 100 ml round bottom flask, substituted acetophenone (30 mmol,1 equiv) and NaH (33 mmol, 1.1 equiv) was dissolved in THF at 0 C. Thecorresponding acid ethyl ester was added and the mixture was stirred at0 C for 30 min. Then, the reaction was stirred at room temperature for12 h. After the reaction was quenched with saturated NH4Cl (50 ml) andextracted with EtOAc (2 × 100 ml), the combined organic layers werewashed with brine (50 ml), dried over Na2SO4, concentrated undervacuum and purified by column chromatography on silica gel to affordthe corresponding product 2.
  • 4
  • [ 7357-70-2 ]
  • [ 4023-81-8 ]
  • [ 109273-53-2 ]
  • [ 94639-15-3 ]
  • 5
  • [ 4023-81-8 ]
  • [ 98078-02-5 ]
  • [ 98078-33-2 ]
  • 6
  • [ 4023-81-8 ]
  • [ 98078-37-6 ]
  • [ 98078-29-6 ]
  • 7
  • [ 4023-81-8 ]
  • [ 95081-19-9 ]
  • (6-Bromo-3-methyl-4H-benzo[1,4]thiazin-2-yl)-(4-bromo-phenyl)-methanone [ No CAS ]
  • 8
  • [ 4023-81-8 ]
  • [ 98078-35-4 ]
  • [ 98078-21-8 ]
  • 9
  • [ 4023-81-8 ]
  • [ 98078-36-5 ]
  • [ 98078-25-2 ]
  • 11
  • [ 4023-81-8 ]
  • [ 137-07-5 ]
  • [ 124453-66-3 ]
  • 12
  • [ 4023-81-8 ]
  • [ 107-91-5 ]
  • [ 109273-56-5 ]
  • [ 109273-58-7 ]
  • 13
  • [ 4023-81-8 ]
  • [ 93168-99-1 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; In dichloromethane; at 20℃; for 0.5h; General procedure: To a solution of 1,3-diketones 1a-g (1.0 mmol) in DCM (10 mL) was added NBS (0.177 g, 1.0 mmol) and mixture was allowed to stir at rt for 30 min. Subsequently, 2-aminopyridine 2 (0.094 g, 1.0 mmol) was added and reaction mixture was maintained at rt with stirring. The reaction was monitored with TLC. On completion of reaction (4 h), excess DCM was distilled off in vacuo and the residue was washed with aq NaHCO3 and extracted with DCM. Organic layers were combined, dried over anhyd. Na2SO4 and excess solvent was distilled off. The residual mass was recrystallized from ethanol and 7a-g was obtained in 71-81% yield.
  • 14
  • [ 99-90-1 ]
  • CH3-COOR (2a-c,f) [ No CAS ]
  • [ 4023-81-8 ]
  • 15
  • [ 4023-81-8 ]
  • [ 1441-85-6 ]
  • 1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone [ No CAS ]
  • (4-bromo-phenyl)-(3-hydroxy-benzo[<i>b</i>]selenophen-2-yl)-methanone [ No CAS ]
  • 2-acetyl-2-(4-bromo-benzoyl)-benzo[<i>b</i>]selenophen-3-one [ No CAS ]
  • 16
  • [ 4023-81-8 ]
  • [ 3306-62-5 ]
  • [ 862420-62-0 ]
  • 17
  • [ 74-85-1 ]
  • [ 4023-81-8 ]
  • [ 53498-48-9 ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine;palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at -196 - 100℃; under 15514.9 Torr; for 12.3333h;Product distribution / selectivity; Example 1 Synthesis of 4-vinylbenzoylacetone: Dimethyl formamide (30 mL), palladium acetate (0.022 g, 0.1 mmol), tri-o-tolyl phosphine (0.060 g, 0.2 mmol), triethylamine (9.1 g, 90 mmol), 4-bromobenzoylacetone (2.41 g, 10 mmol) were added to a 100 mL Parr high pressure reactor with an inner glass liner. The solution was degassed with nitrogen for 10 minutes before the reactor was cooled to -196 C. and ethylene (1.7 g, 61 mmol) was condensed for 20 minutes. The reactor was allowed to warm to room temperature before heating to 100 C. in an oil bath. The pressure was bled off until 300 psi was achieved and the reaction was allowed to proceed for 12 hours. The reaction vessel was cooled to room temperature, the extra pressure bled, and the contents dissolved in water (50 mL) and ether (50 mL). The aqueous phase was made acidic by addition of concentrated hydrochloric acid followed by extraction with ether (2*50 mL). The combined organic phase was rinsed with saturated sodium chloride solution, and the organic phase was dried over magnesium sulfate overnight. The solution was filtered, the solvent was removed by vacuum, and the residue dissolved in chloroform (3 mL). The product was isolated by column chromatography from silica gel (Selecto, mesh size 63-200) with chloroform as eluent. The first band collected resulted in a yellow powder (1.03 g, 55% yield) upon solvent removal. 1H-NMR (200 MHz, 25 C., CDCl3): δ 16.12 (s, 1 H), 7.83 (d, 2 H), 7.45 (d, 2 H), 6.70 (dd, 1 H), 6.17 (s, 1 H), 5.82 (d, 1 H), 5.35 (d, 1 H), 2.20 (s, 3 H).
  • 18
  • [ 6048-21-1 ]
  • [ 67-64-1 ]
  • [ 4023-81-8 ]
  • 19
  • [ 75-15-0 ]
  • [ 4023-81-8 ]
  • [ 500169-91-5 ]
  • 20
  • [ 4023-81-8 ]
  • [ 623-47-2 ]
  • C20H19BrO5 [ No CAS ]
  • C20H19BrO5 [ No CAS ]
  • 21
  • [ 4023-81-8 ]
  • C16H14N2O2S [ No CAS ]
  • 22
  • [ 4023-81-8 ]
  • C19H22N2O3S [ No CAS ]
  • 23
  • [ 4023-81-8 ]
  • C21H19NO3S [ No CAS ]
  • 24
  • [ 4023-81-8 ]
  • C21H20N2O2S [ No CAS ]
  • 25
  • [ 4023-81-8 ]
  • C21H20N2O2S [ No CAS ]
  • 26
  • [ 4023-81-8 ]
  • C23H22N2O3S [ No CAS ]
  • 27
  • [ 4023-81-8 ]
  • C23H22N2O3S [ No CAS ]
  • 28
  • [ 4023-81-8 ]
  • C23H22N2O3S [ No CAS ]
  • 29
  • [ 4023-81-8 ]
  • C21H18ClNO2S [ No CAS ]
  • 30
  • [ 4023-81-8 ]
  • C22H18N2O2S [ No CAS ]
  • 31
  • [ 4023-81-8 ]
  • C22H18F3NO3S [ No CAS ]
  • 32
  • [ 4023-81-8 ]
  • C22H18F3NO3S [ No CAS ]
  • 33
  • [ 4023-81-8 ]
  • C28H25NO3S [ No CAS ]
  • 34
  • [ 4023-81-8 ]
  • C28H25NO3S [ No CAS ]
  • 35
  • [ 4023-81-8 ]
  • C23H21NO3S [ No CAS ]
  • 36
  • [ 4023-81-8 ]
  • C23H21NO3S [ No CAS ]
  • 37
  • [ 4023-81-8 ]
  • C23H21NO3S [ No CAS ]
  • 38
  • [ 4023-81-8 ]
  • C22H19NO3S [ No CAS ]
  • 39
  • [ 4023-81-8 ]
  • C23H21NO4S [ No CAS ]
  • 40
  • [ 4023-81-8 ]
  • C23H21NO4S [ No CAS ]
  • 41
  • [ 4023-81-8 ]
  • C24H23NO4S [ No CAS ]
  • 42
  • [ 4023-81-8 ]
  • C29H25NO4S [ No CAS ]
  • 43
  • [ 4023-81-8 ]
  • C22H20N2O3S [ No CAS ]
  • 44
  • [ 4023-81-8 ]
  • C27H23NO2S [ No CAS ]
  • 45
  • [ 4023-81-8 ]
  • C27H23NO2S [ No CAS ]
  • 46
  • [ 4023-81-8 ]
  • C23H17F6NO2S [ No CAS ]
  • 47
  • [ 4023-81-8 ]
  • C22H21NO3S [ No CAS ]
  • 48
  • [ 4023-81-8 ]
  • C29H25NO2S [ No CAS ]
  • 49
  • [ 4023-81-8 ]
  • C23H20ClNO2S [ No CAS ]
  • 50
  • [ 4023-81-8 ]
  • C23H20FNO2S [ No CAS ]
  • 51
  • [ 4023-81-8 ]
  • C25H23NO4S [ No CAS ]
  • 52
  • [ 4023-81-8 ]
  • C25H23NO4S [ No CAS ]
  • 53
  • [ 4023-81-8 ]
  • C30H24N2O4S [ No CAS ]
  • 54
  • [ 4023-81-8 ]
  • C19H17NO2S2 [ No CAS ]
  • 55
  • [ 4023-81-8 ]
  • C19H17NO2S2 [ No CAS ]
  • 56
  • [ 4023-81-8 ]
  • C19H17NO3S [ No CAS ]
  • 57
  • [ 4023-81-8 ]
  • C20H17NO3S2 [ No CAS ]
  • 58
  • [ 4023-81-8 ]
  • C23H19NO3S [ No CAS ]
  • 59
  • [ 4023-81-8 ]
  • C25H21NO2S [ No CAS ]
  • 60
  • [ 4023-81-8 ]
  • C26H21NO3S [ No CAS ]
  • 61
  • [ 4023-81-8 ]
  • C27H21NO3S [ No CAS ]
  • 62
  • [ 4023-81-8 ]
  • 2-(4-benzo[<i>b</i>]thiophen-3-yl-phenyl)-6-morpholin-4-yl-thiopyran-4-one [ No CAS ]
  • 63
  • [ 4023-81-8 ]
  • 2-morpholin-4-yl-6-(4-naphthalen-1-yl-phenyl)-thiopyran-4-one [ No CAS ]
  • 64
  • [ 4023-81-8 ]
  • 2-[4-(4-methyl-naphthalen-1-yl)-phenyl]-6-morpholin-4-yl-thiopyran-4-one [ No CAS ]
  • 65
  • [ 4023-81-8 ]
  • [ 13114-87-9 ]
  • [ 105-07-7 ]
  • 4-{5-(4-bromobenzoyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With polyphosphoric acid ethyl ester; In tetrahydrofuran; for 20h;Heating / reflux; Example 83; 4- {5- (4-Bromobenzoyl)-6-methyl-2-oxo-1- [3- (trifluoromethyl) phenyl]-1, 2,3, 4-tetrahydropyrimi- din-4-yl} b enzonitril e; 4.23 g (20.74 mmol) N-[3-(trifluoromethyl) phenyl] urea, 2.72 g (20.74 mmol) 4-cyanobenz- aldehyde, 5.00 g (20.74 mmol) 1- (4-bromophenyl) butane-1, 3-dione and 6.5 g polyphosphoric acid ethyl ester are suspended in 50 ml of tetrahydrofuran. The mixture is stirred at reflux for 20 hours. After cooling down to room temperature, the solvent is removed i7l vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethyl acetate mixtures as eluent. Yield: 5.32 g (45% of th.) 'H-NMR (400 MHz, DMSO-d6) : 8 = 1.4 (s, 3H), 5.4 (d, 1H), 7.6-7. 9 (m, 12H), 8.4 (d, 1H) ppm.
  • 66
  • concentrated aqueous ammonium hydroxide [ No CAS ]
  • [ 4023-81-8 ]
  • [ 1488363-22-9 ]
YieldReaction ConditionsOperation in experiment
In methanol; hexane; The intermediate 3-(4-bromophenyl)-1-methyl-3-oxo-1-propenamine, m.p. 126-128 C., 56.8 g, was prepared following the procedure described in Example A-2 using 83 g of <strong>[4023-81-8]1-(4-bromophenyl)-1,3-butanedione</strong>, 750 ml of methanol and 100 ml of concentrated aqueous ammonium hydroxide solution. The solid residue after stripping the reaction mixture to dryness on a rotary evaporator was treated with 500 ml of boiling n-hexane, the mixture allowed to stand at room temperature overnight, and, the product collected and dried at room temperature.
  • 67
  • sodium hexachlorodipalladate [ No CAS ]
  • [ 4023-81-8 ]
  • [ 590419-75-3 ]
  • 68
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 4023-81-8 ]
  • 12BrC6H4COCHCOCH3(1-)*6OH(1-)*6Eu(3+)=Eu6(BrC6H4COCHCOCH3)12(OH)6 [ No CAS ]
  • 70
  • [ 4023-81-8 ]
  • [ 1228180-65-1 ]
  • 71
  • [ 100-42-5 ]
  • [ 4023-81-8 ]
  • [ 1248472-15-2 ]
  • 72
  • [ 4023-81-8 ]
  • [ 201802-67-7 ]
  • [ 1285686-71-6 ]
  • 73
  • [ 4023-81-8 ]
  • 3-amino-5-hydrazinopyrazole dihydrochloride [ No CAS ]
  • [ 586-76-5 ]
  • [ 1312998-64-3 ]
  • [ 145353-53-3 ]
YieldReaction ConditionsOperation in experiment
50%; 34% In water; for 4h;pH 0.8;Reflux; General procedure: To H2O (20 ml) were added 3(5)-amino-5(3)-hydrazinopyrazole dihydrochloride (5) (0.93 g, 0.005 mol) and CH3COCH2COC6H5 (6b) (0.81 g, 0.005 mol). This reaction mixture was found to have pH 0.8 at 25 C. Then the reaction mixture was refluxed for 4 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature and extracted using 2 × 30 ml portions of ethyl acetate. The combined organic layers were successively washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a residual mass. The residue obtained on cooling was found to be a mixture of three products as predicted by TLC and 1H NMR spectrum. The residue was column chromatographed over silica gel (100-200 mesh) using petroleum ether followed by petroleum ether/CHCl3 of increasing polarity as eluent to yield three compounds- benzoic acid 10b m.p. 120-121 C (lit. [35] m.p. 121-123 C) in the first fraction, followed by 3-methyl-5-phenyl-1H-pyrazole (9b) m.p. 129-130 C; (lit. [26], [27] and [28] m.p. 128 C); yield 8% and finally 2-(3'-methyl-5'-phenylpyrazol-1'-yl)-5-methyl-7-phenylpyrazolo[1,5-a]pyrimidine (7b).
  • 74
  • [ 4023-81-8 ]
  • [ 100-97-0 ]
  • [ 1338356-17-4 ]
  • 75
  • [ 4023-81-8 ]
  • [ 623-27-8 ]
  • [ 17356-08-0 ]
  • [ 57-13-6 ]
  • [ 1369963-63-2 ]
  • 76
  • [ 4023-81-8 ]
  • [ 100-52-7 ]
  • [ 1422578-22-0 ]
  • 77
  • [ 4023-81-8 ]
  • [ 1443156-68-0 ]
  • [ 1443156-83-9 ]
  • 78
  • [ 4023-81-8 ]
  • [ 1488363-22-9 ]
  • 79
  • [ 79-20-9 ]
  • [ 99-90-1 ]
  • [ 4023-81-8 ]
YieldReaction ConditionsOperation in experiment
95.5% In a 50 mL round bottom flask, a stirred solution of 4-bromo acetophenone (2.0 g,10.10 mmol) in THF (10 mL) was treated with NaH (60% dispersion, 0.80 g, 20.20 mmol) at0 C under nitrogen atmosphere. The resulting reaction mixture was stuffed for 2 h at RT andtreated with methyl acetate (2.23 g, 30.15 mmol) at 0 C. The resulting reaction mixture wasstirred at RT for 12 h. Upon completion of the reaction (TLC), the reaction mixture was diluted with cold water and extracted with EtOAc (2 x 30 mL). The organic extract was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to get the crude residue. The residue obtained was triturated with n-pentane (2 x 20 mL) to afford the title compound. Yield: 2.31 g (95.5%).‘H NMR (400 MHz, CDCl3) ö 7.74 (d, J= 8.8 Hz, 2H), 7.58 (d, J= 8.4 Hz, 2H), 6.14 (s, 1H), 2.20 (s, 3H).LCMS (ESI+, m/z): 241.2, 243.2 (M+H).
  • 80
  • [ 75-15-0 ]
  • [ 4023-81-8 ]
  • [ 106-93-4 ]
  • [ 76212-25-4 ]
  • 81
  • [ 4023-81-8 ]
  • [ 4392-24-9 ]
  • C19H17BrO2 [ No CAS ]
  • 82
  • [ 1122-91-4 ]
  • [ 67-64-1 ]
  • [ 4023-81-8 ]
YieldReaction ConditionsOperation in experiment
81% With tert.-butylhydroperoxide; di-tert-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; at 120℃; for 24h; General procedure: Under air atmosphere, aldehydes (0.3 mmol), TBAI (0.2 equiv),TBHP (2.0 equiv), DTBP (2.0 equiv), p-TsOH (0.1 equiv), and acetoneor other ketones (2 mL) were added to a screw-capped vial.The reaction vial was placed in a temperature-controlled aluminum-heating block set at 120 C. The reaction progress wasmonitored by TLC. After the completion of the reaction, the vialwas removed from the heating block and was left to cool to ambienttemperature. The solution was filtered through a short columnof silica gel and washed with EtOAc. The filtrate was concentratedunder reduced pressure to leave a crude product, which was purifiedby flash column chromatography on silica gel with petroleumether/EtOAc as an eluent to give the desired product
81% With tert.-butylhydroperoxide; di-tert-butyl peroxide; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; at 120℃; for 24h; To a 25 mL pressure-resistant reaction tube was added 2 mL of acetone, p-bromobenzaldehyde (55.2 mg, 0.3mmol), tert-butyl hydroperoxide (83 mg, 2.0 eq.), di-tert-butyl peroxide (88 mg, 2.0 eq.), tetrabutylammonium iodide (22 mg, 0.2 eq.), p-toluenesulfonic acid (5 mg, 0.1 eq.). In a 120 C oil bath, under magnetic stirring, react for 24 hours. To be after the reaction is completed, pressure reducing evaporate most of the solvent, petroleum ether/ethyl acetate (20:1) as leaching of the remaining column chromatography separation and purification of the mixed liquid, that is a required product is obtained, as a yellow solid, 58.3 mg, yield 81%.
  • 83
  • [ 4023-81-8 ]
  • [ 135-02-4 ]
  • (E)-1-(4-bromophenyl)-2-(2-methoxybenzylidene)butane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.3% With piperidine; acetic acid; In ethanol; for 48h;Molecular sieve; Reflux; In a 50 mL round bottom flask, a solution of (4-bromophenyl)butane-1,3-dione (1.0 g, 4.16 mmol) in EtOH (30 mL) was treated with 2-methoxybenzaldehyde (0.564 g, 4.16 mmol), piperidine (0.155 g, 1.82 mmol), AcOH (0.327 g, 5.46 mmol) and 4 A molecular sieves (--1.5 g) at RT. The reaction mixture was refluxed for 2 days. Upon completion of reaction (TLC), the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with cold water and extracted with EtOAc (2 x 300 mL). The combined organic extract was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the residue obtained was purified by silica gel column chromatography (elution, 20% EtOAc in hexanes) to yield the title compound. Yield: 1.10 g (74.3%).‘H NMR (300 MHz, CDCl3) ö 8.13 (s, 1H), 7.72 (d, J= 9.0 Hz, 2H), 7.51 (d, J= 8.1 Hz, 2H), 7.26 (m, 1H), 7.15 (d, J= 9.3 Hz, 1H), 6.82 (d, J= 8.1 Hz, 1H), 6.73 (t, J= 8.1 Hz, 1H),3.78 (s, 3H), 2.44 (s, 3H). LCMS (ESI+, m/z): 358.9, 360.9 (M+H).
  • 84
  • [ 4023-81-8 ]
  • [ 74-88-4 ]
  • 1-(4-bromophenyl)-2-methylbutane-1,3-dione [ No CAS ]
  • 86
  • [ 4023-81-8 ]
  • 2,2-dibromo-1-(4-bromophenyl)butane-1,3-dione [ No CAS ]
  • 87
  • [ 4023-81-8 ]
  • [ 873-55-2 ]
  • [ 41024-55-9 ]
  • 88
  • [ 4023-81-8 ]
  • [ 122-39-4 ]
  • (4-bromophenyl)(5-(diphenylamino)-2-methyl-1-phenyl-1H-indol-3-yl)methanone [ No CAS ]
  • 89
  • [ 4023-81-8 ]
  • [ 271-58-9 ]
  • 2-methyl-3-(p-bromo)benzoylquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With oxygen; caesium carbonate; copper(I) bromide; at 130℃; for 24.0h;Schlenk technique; <strong>[271-58-9]2,1-<strong>[271-58-9]benzisoxazole</strong></strong> (0.3 mmol, 44.7 mg), 1-(3-bromophenyl)-1,3-butanedione (0.6 mmol, 144.6 mg), copper bromide (0.045 mmol, 10.0 mg) and cesium carbonate (0.6 mmol, 195.5 mg) were added to a 25 ml Schlenk tube under reduced pressure.The reaction tube was replaced with oxygen three times. Hexafluoroisopropanol (2 ml) was added and stirred at 130 C for 24 hours. After the completion of the reaction, a 200-mesh column chromatography silica gel was added, and the solvent was evaporated under reduced pressure. The crude product was subjected to silica gel column chromatography and washed with petroleum ether and ethyl acetate ( petroleum ether: ethyl acetate = 20:1). Detach, with TLC elution tracking detection,The eluate containing the desired product was collected, and the desired product eluent was combined and evaporated to give a quinoline compound of the formula i above, yield 88%.This material is a reddish yellow solid.
  • 90
  • [ 3153-26-2 ]
  • [ 4023-81-8 ]
  • C20H16Br2O5V [ No CAS ]
  • 91
  • [ 4547-64-2 ]
  • [ 4023-81-8 ]
  • (4-bromophenyl)(1-((4-methoxyphenyl)sulfonyl)-5-methyl-1H-1,2,3-triazol-4-yl)methanone [ No CAS ]
  • 92
  • [ 4023-81-8 ]
  • [ 150-76-5 ]
  • [ 177915-49-0 ]
  • 93
  • [ 4023-81-8 ]
  • [ 613-03-6 ]
  • 2-(4-bromophenyl)-6,7-dihydroxy-4-methyl-1-benzopyrylium perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% The pyrogallol A (2.52 g, 10 mmol)and benzoylacetone (1.62 g, 10 mmol) were dissolved in a 50 cm3round bottom flask in 10 cm3 of glacial acetic acid when heated(~60 C), then it was cooled to room temperature. After that 5 ml of50% perchloric acid was added. The reaction mixture was boiledwith a reflux for 40 min. After cooling to room temperature, thebrown crystalline precipitate was filtered out on the Schott filter under vacuum and washed twice with distilled water in portions of10 ml. The yield is 68%.
  • 94
  • [ 4023-81-8 ]
  • [ 4559-70-0 ]
  • [ 19797-85-4 ]
  • [ 1733-52-4 ]
  • 95
  • [ 4023-81-8 ]
  • [ 67-68-5 ]
  • (4-hydroxy-6-p-bromophenyl-1,3-phenylene)-1-ethanone-3-p-bromophenylmethanone [ No CAS ]
  • (4-hydroxy-6-methyl-1,3-phenylene)bis(p-bromophenylmethanone) [ No CAS ]
YieldReaction ConditionsOperation in experiment
26%; 58% With copper(ll) sulfate pentahydrate; at 130℃; for 12h; General procedure: A 25 mL of dried round-bottom flask was charged with 1-phenylbutane-1,3-dione 1a (0.5 mmol), CuSO4·5H2O (10 mol%) and DMSO (2 mL) at 130 C for 6 h. After completion of the reaction (monitored by TLC), the water (10 mL) was added. The aqueous solution was extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (2×10 mL) and dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether/ethyl acetate = 15:1) to give a pure sample of 2a and 2a′.
  • 96
  • [ 4023-81-8 ]
  • [ 333-20-0 ]
  • 4-acetyl-5-(4-bromophenyl)thiazol-2(3H)-one [ No CAS ]
  • 97
  • [ 4023-81-8 ]
  • [ 824-79-3 ]
  • [ 1576-35-8 ]
  • 5-(4-bromophenyl)-3-methyl-1,4-ditosyl-1H-pyrazole [ No CAS ]
  • 98
  • [ 4023-81-8 ]
  • [ 948293-34-3 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate; In methanol; for 2h;Reflux; Inert atmosphere; General procedure: In a 100 ml round bottom flask equipped with a condenser tube,corresponding intermediate substrate 2 (10 mmol, 1 equiv) andN2H4H2O (10 mmol, 1 equiv) was dissolved in CH3OH. The reactionwas reflux for 2 h. After the reaction was completed, the organic solventwas removed under vacuum, the residue was purified by column chromatographyon silica gel to afford the corresponding product 3.
  • 99
  • [ 20300-02-1 ]
  • [ 4023-81-8 ]
  • C15H10BrNOS2 [ No CAS ]
  • 100
  • [ 96-45-7 ]
  • [ 4023-81-8 ]
  • 2-(4-bromobenzoyl)-3-methyl-5,6-dihydroimidazo[2,1-b]thiazole [ No CAS ]
  • 101
  • [ 4023-81-8 ]
  • [ 42202-95-9 ]
  • (4-bromophenyl)(3-(4-fluorophenyl)-5-methylisoxazol-4-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine In methanol; lithium hydroxide monohydrate at 20℃; for 2h; General synthetic procedure forthe [3 + 2]-cycloaddition reaction General procedure: To a solution of the 1,3-diketone, β-ketoester, or β-ketoamide(0.5 mmol, 1 equiv) in methanol was added water, phenylhydroximoyl chloride (1 equiv), and DIPEA (3 equiv) at roomtemperature (total volume of methanol and water = 15 mL; 95%water, 5% methanol). The reaction mixture was stirred for 1-2 huntil all of the starting materials were consumed (TLC, 10%ethyl acetate in hexanes). After the reaction was complete, theproduct was extracted with ethyl acetate, dried with Na2SO4,concentrated under reduced pressure, and purified via columnchromatography (ethyl acetate/hexanes).
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkyl Halide Occurrence • Alkylation of Aldehydes or Ketones • Alkylation of an Alkynyl Anion • Alkylation of Enolate Ions • An Alkane are Prepared from an Haloalkane • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deoxygenation of the Carbonyl Group • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • Diorganocuprates Convert Acyl Chlorides into Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Isomerization of β, γ -Unsaturated Carbonyl Compounds • Ketone Synthesis from Nitriles • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Methylation of Ammonia • Methylation of Ammonia • Michael Addition • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Strecker Synthesis • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • The Reaction of Alkynyl Anions with Carbonyl Derivatives • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vilsmeier-Haack Reaction • Williamson Ether Syntheses • Wittig Reaction • Wolff-Kishner Reduction
Historical Records
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