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[ CAS No. 51483-92-2 ] {[proInfo.proName]}

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Chemical Structure| 51483-92-2
Chemical Structure| 51483-92-2
Structure of 51483-92-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51483-92-2 ]

CAS No. :51483-92-2 MDL No. :MFCD00239369
Formula : C9H5BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XVNBWGGBXOJIDR-UHFFFAOYSA-N
M.W : 225.04 Pubchem ID :548522
Synonyms :

Safety of [ 51483-92-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51483-92-2 ]

* 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 [ 51483-92-2 ]

[ 51483-92-2 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 623-73-4 ]
  • [ 51483-92-2 ]
  • (1S,1aS,7aS)-5-Bromo-7-oxo-1,1a,7,7a-tetrahydro-2-oxa-cyclopropa[b]naphthalene-1-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 6-bromo-1-benzopyran-4(4H)-one With trimethylsilyl trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate) at 20℃; for 0.5h; Stage #2: diazoacetic acid ethyl ester In dichloromethane at 0℃;
  • 2
  • [ 51483-92-2 ]
  • [ 1826-67-1 ]
  • 6-bromo-2-vinylchroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 6-bromo-1-benzopyran-4(4H)-one With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Stage #2: vinyl magnesium bromide In tetrahydrofuran; dichloromethane at -78℃; for 0.5h; Stage #3: With ammonium chloride In tetrahydrofuran; dichloromethane; water at -78 - 20℃;
  • 3
  • [ 51085-91-7 ]
  • [ 51483-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 52 percent / K2CO3 / acetone / 8 h / Heating 2: dimethylformamide / 8 h / Heating
  • 4
  • [ 51483-92-2 ]
  • [ 171860-66-5 ]
  • [ 1160556-52-4 ]
YieldReaction ConditionsOperation in experiment
With 2′-(dicyclohexylphophanyl)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine; palladium diacetate In tetrahydrofuran; toluene at 0 - 20℃; Inert atmosphere;
  • 5
  • [ 30069-31-9 ]
  • [ 51483-92-2 ]
  • [ 1186206-82-5 ]
YieldReaction ConditionsOperation in experiment
26% With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 80℃; for 48h; Inert atmosphere;
  • 6
  • [ 51483-92-2 ]
  • [ 98-80-6 ]
  • 6-bromo-2-phenylchroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; 2-((S)-2-((R)-tert-butylsulfinyl)phenylsulfinyl)-1,3,5-trimethylbenzene; potassium hydrogencarbonate In water; toluene at 40℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 7
  • [ 1121-60-4 ]
  • [ 51483-92-2 ]
  • [ 1309184-54-0 ]
YieldReaction ConditionsOperation in experiment
80% With N,N,N'N'-tetramethyl-1,3-propanediamine In tetrahydrofuran; water at 20℃; for 36h;
  • 8
  • [ 1122-72-1 ]
  • [ 51483-92-2 ]
  • [ 1309184-62-0 ]
YieldReaction ConditionsOperation in experiment
62% With N,N,N'N'-tetramethyl-1,3-propanediamine In tetrahydrofuran; water at 20℃; for 36h;
  • 9
  • [ 5470-96-2 ]
  • [ 51483-92-2 ]
  • [ 1309184-69-7 ]
YieldReaction ConditionsOperation in experiment
65% With N,N,N'N'-tetramethyl-1,3-propanediamine In tetrahydrofuran; water at 20℃; for 36h;
  • 10
  • [ 51483-92-2 ]
  • [ 98-80-6 ]
  • [ 1277188-80-3 ]
  • (S)-6-bromo-2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 81% 2: 3% With [Rh(OH)(cod)]2; (S)-MeO-F12-BIPHEP In dichloromethane; water at 35℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 11
  • [ 100-42-5 ]
  • [ 51483-92-2 ]
  • [ 1260485-39-9 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Inert atmosphere; diastereoselective reaction;
  • 12
  • [ 49660-57-3 ]
  • [ 51483-92-2 ]
  • 13
  • [ 51483-92-2 ]
  • [ 115-18-4 ]
  • [ 1260485-34-4 ]
YieldReaction ConditionsOperation in experiment
74% With potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 0.416667h; Inert atmosphere; diastereoselective reaction;
  • 14
  • [ 51483-92-2 ]
  • [ 3054-95-3 ]
  • [ 1260485-32-2 ]
YieldReaction ConditionsOperation in experiment
28% With tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 7h; Inert atmosphere;
  • 15
  • [ 51483-92-2 ]
  • [ 3054-95-3 ]
  • [ 1260485-32-2 ]
  • [ 1260485-33-3 ]
YieldReaction ConditionsOperation in experiment
1: 53% 2: 10% With potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 1.5h; Inert atmosphere; diastereoselective reaction;
  • 16
  • [ 51483-92-2 ]
  • [ 140-88-5 ]
  • [ 1260485-31-1 ]
YieldReaction ConditionsOperation in experiment
92% With potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 0.416667h; Inert atmosphere; diastereoselective reaction;
  • 17
  • [ 93670-18-9 ]
  • [ 51483-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: polyphosphoric acid / 1 h / Heating 2: iodine / dimethyl sulfoxide / 2 h / Reflux
  • 18
  • [ 51483-92-2 ]
  • [ 141-32-2 ]
  • [ 1321627-98-8 ]
YieldReaction ConditionsOperation in experiment
93% With copper diacetate; palladium diacetate; silver carbonate; Trimethylacetic acid at 120℃; for 11h; Inert atmosphere;
  • 19
  • (E)-1-(5-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one [ No CAS ]
  • [ 51483-92-2 ]
YieldReaction ConditionsOperation in experiment
94% With chloro-trimethyl-silane In N,N-dimethyl-formamide at 90 - 120℃; Inert atmosphere;
  • 20
  • [ 1004-40-6 ]
  • [ 51483-92-2 ]
  • [ 1354628-08-2 ]
  • 21
  • [ 1131-18-6 ]
  • [ 51483-92-2 ]
  • [ 1354628-39-9 ]
YieldReaction ConditionsOperation in experiment
92% With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere; regioselective reaction;
  • 22
  • [ 51483-92-2 ]
  • 1-methyl-3-phenyl-4-amino-4-imidazoline-2-thione [ No CAS ]
  • [ 1354627-95-4 ]
YieldReaction ConditionsOperation in experiment
76% With chloro-trimethyl-silane In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere; regioselective reaction;
  • 23
  • [ 51483-92-2 ]
  • [ 60-34-4 ]
  • [ 1354787-25-9 ]
YieldReaction ConditionsOperation in experiment
44% With ethanol; boron trifluoride diethyl etherate for 22h; Reflux; 89 To a suspension of 6-bromochromone (1.58 g, 0.0070 mol) in ethanol (30 mL) was added methylhydrazine (0.41 mL, 0.0077 mol) and boron trifluoride etherate (1.15 mL, 0.0091 mol). The reaction was heated to reflux for 22 hours. After cooling, the reaction was concentrated in vacuo and the residue purified by automated flash column chromatography using a 0-100% ethyl acetate/hexanes gradient. This provided the title compound (0.79 g, 44%) as a light yellow solid.1HNMR (400 MHz, d6-DMSO): δ 3.70 (s, 3H), 6.30 (d, 1H), 6.96 (d, 1H), 7.36 (d, 1H), 7.47 (m, 2H), 10.28 (br s, 1H).LCMS Rt=1.58 minutes MS m/z 253 [MH]+.
  • 24
  • [ 51483-92-2 ]
  • [ 1354786-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ethanol; boron trifluoride diethyl etherate / 22 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h 2.2: 3 h 3.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4.5 h / Inert atmosphere; Reflux 3.2: 1 h
  • 25
  • [ 51483-92-2 ]
  • [ 1354786-25-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ethanol; boron trifluoride diethyl etherate / 22 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h 2.2: 3 h 3.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 4.5 h / Inert atmosphere; Reflux 3.2: 1 h
  • 26
  • [ 51483-92-2 ]
  • [ 106-51-4 ]
  • [ 1384433-44-6 ]
YieldReaction ConditionsOperation in experiment
93% With silver(I) acetate; palladium diacetate; Trimethylacetic acid In 1,4-dioxane at 100℃; Inert atmosphere;
  • 27
  • [ 51483-92-2 ]
  • 6-bromochroman-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With formic acid; C31H35ClN2O2RhS(1-); sodium formate In water at 60℃; for 3h; Inert atmosphere; optical yield given as %ee; stereoselective reaction;
  • 28
  • [ 51483-92-2 ]
  • [ 98-80-6 ]
  • [ 1218-80-0 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 6-bromo-1-benzopyran-4(4H)-one; phenylboronic acid With iron(III) trifluoromethanesulfonate; palladium diacetate; Trimethylacetic acid at 60℃; under air; Stage #2: With potassium nitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone
61% Stage #1: 6-bromo-1-benzopyran-4(4H)-one; phenylboronic acid With iron(III) trifluoromethanesulfonate; palladium diacetate; Trimethylacetic acid at 60℃; for 24h; Stage #2: With potassium nitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone for 6h;
  • 29
  • [ 51483-92-2 ]
  • [ 103885-22-9 ]
  • [ 1393879-94-1 ]
YieldReaction ConditionsOperation in experiment
92% With potassium phosphate; chloro-(2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl)[2-(2-amino-1,1-biphenyl)]palladium(II) In tetrahydrofuran; water at 40℃; for 2h; Inert atmosphere;
  • 30
  • [ 1003-09-4 ]
  • [ 51483-92-2 ]
  • [ 1453841-23-0 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 2-bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: 6-bromo-1-benzopyran-4(4H)-one With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); XPhos In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere;
  • 31
  • [ 51483-92-2 ]
  • [ 115-19-5 ]
  • [ 1446428-52-9 ]
YieldReaction ConditionsOperation in experiment
48% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine at 70℃; for 1.5h; Inert atmosphere;
  • 32
  • [ 51483-92-2 ]
  • [ 536-74-3 ]
  • [ 1446428-45-0 ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine at 70℃; for 4.5h; Inert atmosphere;
  • 33
  • [ 51483-92-2 ]
  • [ 1066-54-2 ]
  • [ 1446428-48-3 ]
YieldReaction ConditionsOperation in experiment
76% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine at 70℃; for 0.5h; Inert atmosphere;
  • 34
  • [ 1271-51-8 ]
  • [ 51483-92-2 ]
  • (E)-6-ferrocenylvinyl-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 95℃; for 19h; Schlenk technique; 4.2 General procedure for the synthesis of bioconjugates 4-6 General procedure: A deoxygenated mixture of vinylferrocene (170mg, 0.80mmol), K2CO3 (1.50g, 11mmol), tetrabutylammonium bromide (1.19g, 3.70mmol), bromochromone (0.66mmol) and Pd(OAc)2 (20mg, 0.09mmol) in DMF (23ml) was heated at 95°C for 19h. After cooling to r. t. the reaction mixture was evaporated to dryness. Solid residue was dissolved in chloroform and extracted several times with water. The organic phase was dried with MgSO4, filtered and the solvent was removed from the filtrate in vacuo. The residue was subjected to chromatography on SiO2 (eluent: CHCl3/methanol, 50:2). Finally the analytically pure products were obtained after recrystallization from chloroform/n-hexane mixture.
  • 35
  • [ 51483-92-2 ]
  • [ 610-66-2 ]
  • 4-bromo-2-(9H-pyrido[2,3-b]indol-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With acetic acid; triethylamine; zinc for 4h; Reflux;
  • 36
  • [ 51483-92-2 ]
  • [ 927-77-5 ]
  • [ 1504391-17-6 ]
YieldReaction ConditionsOperation in experiment
11.42 g Stage #1: 6-bromo-1-benzopyran-4(4H)-one With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Stage #2: n-propylmagnesium bromide In tetrahydrofuran; dichloromethane at -78 - 20℃; for 1h; Preparation Example 92 To a solution of 6-bromo-4H-chromen-4-one (12g, 53 mmol) in CH2Ch (24mL)was added TMSOTf (12.5mL, 69.18mmol) at ambient temperature. After stirring for 1 hour,THF (210mL) was added to the mixture at ambient temperature and cooled to -78 oc. To themixture was added n-propylmagnesium bromide (1.05M solution in THF, 66mL, 69mmol).After stirring for 1 hour at -78 °C, 1M aqueous NH4Cl was added to the mixture. The mixturewas warmed to ambient temperature and stirred overnight. The organic and the aqueous layerswere separated, and the organic layer was dried over Na2S04, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silicagel column chromatography(EtOAc-hexane, a linear gradient of EtOAc from 0 to 10%) to afford6-bromo-2-propyl-2,3 -dihydro-4 H -chromen -4-one ( 11.42g).
  • 37
  • [ 51483-92-2 ]
  • [ 110-82-7 ]
  • [ 1012781-44-0 ]
YieldReaction ConditionsOperation in experiment
45% With sodium azide; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃;
  • 38
  • [ 51483-92-2 ]
  • [ 501-65-5 ]
  • [ 1619229-16-1 ]
YieldReaction ConditionsOperation in experiment
82% With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper diacetate; acetic acid In 1,2-dichloro-ethane at 100℃; stereoselective reaction;
  • 39
  • [ 51483-92-2 ]
  • 2,3-difluoro-6-bromo-4-chromanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With fluorine In ethanol; chloroform; trichlorofluoromethane at -78℃; Inert atmosphere;
  • 40
  • [ 51483-92-2 ]
  • C8H15IZn*LiCl [ No CAS ]
  • 6-(6-methylhept-5-en-2-yl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 2′-(dicyclohexylphophanyl)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine; C13H13NO3PdS In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Inert atmosphere;
  • 41
  • [ 51483-92-2 ]
  • [ 110-82-7 ]
  • 6-bromo-2-cyclohexylchroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With di-tert-butyl peroxide at 120℃; for 24h; Sealed tube;
  • 42
  • [ 51483-92-2 ]
  • [ 287-92-3 ]
  • 6-bromo-2-cyclopentylchroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With di-tert-butyl peroxide at 120℃; for 24h; Sealed tube;
  • 43
  • [ 51483-92-2 ]
  • [ 291-64-5 ]
  • 6-bromo-2-cycloheptylchroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With di-tert-butyl peroxide at 120℃; for 24h; Sealed tube;
  • 44
  • [ 51483-92-2 ]
  • [ 292-64-8 ]
  • 6-bromo-2-cyclooctylchroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With di-tert-butyl peroxide at 120℃; for 24h; Sealed tube;
  • 45
  • [ 288-88-0 ]
  • [ 51483-92-2 ]
  • 6-bromo-2-(1H-1,2,4-triazol-1-yl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With iodine; potassium carbonate In N,N-dimethyl-formamide at 80℃; regioselective reaction;
  • 46
  • [ 1271-47-2 ]
  • [ 51483-92-2 ]
  • 6-(1-ferrocenylethynyl)chromone [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 75℃; for 18h; Schlenk technique; Inert atmosphere; Synthesis of 6-(1-ferrocenylethynyl)chromone 14 A deoxygenated mixture of ethynylferrocene (210 mg, 1.00 mmol), triethylamine (15 ml), N,N-dimethylformamide (5 ml), 6-bromochromone (150 mg, 0.67 mmol), copper (I) iodide (2.0 mg, 0.01 mmol), triphenylophosphine (5 mg, 0.02 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol) was heated at 75 °C for 18 h. After cooling to r. t. the reaction mixture was evaporated to dryness. The solid residue was dissolved in chloroform and subjected to column chromatography on silica gel with CHCl3. The main, orange-red fraction was collected, evaporated to dryness and subjected to column chromatography on silica gel with CH2Cl2 followed by crystallization from a CHCl3/n-hexane mixture. Complex 14 was obtained as an orange-red solid in a yield of 210 mg, 89% yield. 1H NMR (600 MHz, CDCl3): δ = 8.31 (s, 1H, H-5), 7.84 (d, JH,H = 6.0 Hz,1H, H-2), 7.72 (d, JH,H = 7.8 Hz,1H, H-7), 7.41 (d, JH,H = 8.4 Hz,1H, H-8), 6.34 (d, JH,H = 6.0 Hz,1H, H-3), 4.54 (s, 2H, α-C5H4), 4.28 (s, 2H, β-C5H4), 4.27 (s, 5H, C5H5). 13C NMR (150 MHz, CDCl3): δ = 176.8, 155.5, 155.1, 136.2, 128.6, 124.9, 121.6, 120.1, 118.3, 113.1, 89.8, 84.1, 71.5, 70.0, 69.0. MS (EI, 70 eV): m/z = 354 (M+). HRMS: m/z = 354.03441 (Calc. for C21H14O2Fe: 354.03433). FTIR (KBr ν [cm-1]): 2225(C≡C), 1646(C=O), 1635 (C=O), 1612 (C=O), 1439. Anal. Calcd for C21H14O2Fe: C, 71.21; H, 3.98. Found: C, 71.22; H, 3.86%.
  • 47
  • [ 51483-92-2 ]
  • [ 106-45-6 ]
  • 6-bromo-3-(p-tolylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With ammonium iodide In N,N-dimethyl-formamide at 135℃; for 15h; Green chemistry; regioselective reaction;
  • 48
  • [ 51483-92-2 ]
  • [ 108-98-5 ]
  • 6-bromo-3-(phenylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With ammonium iodide In N,N-dimethyl-formamide at 135℃; for 15h; Green chemistry; regioselective reaction;
  • 49
  • [ 51483-92-2 ]
  • [ 80-17-1 ]
  • 6-bromo-3-(phenylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With ammonium iodide In N,N-dimethyl acetamide at 135℃; for 24h; Sealed tube; regioselective reaction;
  • 50
  • [ 51483-92-2 ]
  • [ 67-68-5 ]
  • 6-bromo-3-(methylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With ammonium iodide In acetonitrile at 135℃; for 24h; Sealed tube; regioselective reaction;
  • 51
  • [ 51483-92-2 ]
  • [ 1300602-28-1 ]
  • 0.97C9H5BrO2*C50H36N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hexane at 45℃; 2.2.1. Loading of guest molecules and calculating the binding ratios General procedure: The solvent was removed from freshly recrystallized host 1*DMSO by TGA or by heating samples (50 mg) at 120°C 1 h. Next empty host 1 crystals (15 mg) were soaked in solutions containing the guest (1 mM). Loading studies of chromone, 6-fluorochromone, and 6-bromochromone were carried out in hexane at 45°C, while 7-hydroxy-4-chromone and 3-cyanochromone were carried out at rt in acetonitrile. The uptake of the guests into the host 1 was monitored through the change in the absorbance of the solution over time (from 0 to 3 h). A standard Beer-Lambert curve was generated for each guest and used to calculate the binding ratios (see Figs. S6-S10, SI).
  • 52
  • [ 51483-92-2 ]
  • [ 98-09-9 ]
  • 6-bromo-3-(phenylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With ammonium iodide In N,N-dimethyl-formamide at 130℃; for 20h; Sealed tube; regioselective reaction;
  • 53
  • [ 51483-92-2 ]
  • [ 98-59-9 ]
  • 6-bromo-3-(p-tolylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With ammonium iodide In N,N-dimethyl-formamide at 130℃; for 20h; Sealed tube; regioselective reaction;
  • 54
  • [ 51483-92-2 ]
  • [ 2999-46-4 ]
  • C14H12BrNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; silver carbonate In N,N-dimethyl-formamide at 100℃; for 1h;
  • 55
  • [ 51483-92-2 ]
  • [ 873-55-2 ]
  • 6-bromo-3-(phenylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With ammonium iodide In N,N-dimethyl-formamide at 135℃; for 20h; Sealed tube; regioselective reaction;
  • 56
  • [ 51483-92-2 ]
  • [ 824-79-3 ]
  • 6-bromo-3-(p-tolylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With ammonium iodide In N,N-dimethyl-formamide at 135℃; for 20h; Sealed tube; regioselective reaction;
  • 57
  • [ 51483-92-2 ]
  • [ 54856-82-5 ]
  • 6-(1-(pyridin-2-yl)vinyl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; nickel(II) acetate tetrahydrate; potassium carbonate In toluene at 130℃; for 24h; Inert atmosphere; Sealed tube;
  • 58
  • [ 51483-92-2 ]
  • [ 10365-98-7 ]
  • (R)-6-bromo-2-(3-methoxyphenyl)chroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.9% Stage #1: 3-methoxyphenylboronic acid With ammonium hexafluorophosphate; palladium(II) trifluoroacetate; 2-[(S)-4,5-dihydro-4-tert-butyl-1,3-oxazol-2-yl]pyridine In 1,2-dichloro-ethane for 0.0833333h; Stage #2: 6-bromo-1-benzopyran-4(4H)-one With water In 1,2-dichloro-ethane at 60℃; for 16h; 47A Example 47A (i?)-6-bromo-2-(3-methoxyphenyl)chroman-4-one Example 47A (i?)-6-bromo-2-(3-methoxyphenyl)chroman-4-one A 20 mL vial was charged with bis(2,2,2-trifluoroacetoxy)palladium (0.295 g, 0.889 mmol), (5)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole (0.218 g, 1.066 mmol), ammonium hexafluorophosphate(V) (0.869 g, 5.33 mmol) and (3-methoxyphenyl)boronic acid (2.70 g, 17.77 mmol) were stirred in dichloroethane (5 mL) for 5 minutes, and a pale yellow color was observed. To this suspension was added 6-bromo-4H-chromen-4-one (CAS 51483-92-2) (2.0 g, 8.89 mmol) and water (0.256 mL, 14.19 mmol) and the sides of the vial washed with more dichloroethane (5 mL). The vial was capped and the mixture stirred at 60 °C for 16 hours. The mixture was filtered through a plug of silica gel and celite and eluted with ethyl acetate to give a light yellow color solution. The solvent was removed under reduced pressure and the crude material was chromatographed on a 40 g silica gel cartridge, eluting with a gradient of 5-50 % ethyl acetate/heptanes to provide the title compound (2.10 g, 6.30 mmol, 70.9 % yield). 1H NMR (400 MHz, CDC13) δ 8.04 (d, J= 2.6 Hz, 1H), 7.58 (dd, J= 8.9, 2.6 Hz, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.08 - 6.87 (m, 4H), 5.45 (dd, J= 13.1, 3.1 Hz, 1H), 3.84 (s, 3H), 3.07 (dd, J = 17.0, 13.1 Hz, 1H), 2.91 (dd, J= 17.0, 3.1 Hz, 1H).
  • 59
  • [ 51483-92-2 ]
  • methyl 2-((E)-6-bromo-4-(((R)-tert-butylsulfinyl)imino)chroman-2-yl)-2-methylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 2,6-di-tert-butyl-4-methylpyridine / toluene / 1 h / 60 °C / Inert atmosphere 2.1: (R)-2,6-di(naphthalen-2-yl)-3,5-dihydro-4H-dinaphtho[2,1-c:1',2'-e]silepine-4,4-diol / acetone; toluene / 0.17 h / -78 °C 2.2: 4 h / -78 °C 3.1: tetramethoxytitanium / tetrahydrofuran / 48 h / Inert atmosphere; Reflux
  • 60
  • [ 51483-92-2 ]
  • C26H29F6O2Si(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / Reflux 2: 2,6-di-tert-butyl-4-methylpyridine / toluene / 1 h / 60 °C / Inert atmosphere
  • 61
  • [ 51483-92-2 ]
  • [ 73852-19-4 ]
  • 6-(3,5-bis(trifluoromethyl)phenyl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water Reflux;
  • 62
  • [ 51483-92-2 ]
  • [ 80522-42-5 ]
  • C18H26BrO2Si(1+)*CF3O3S(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,6-di-tert-butyl-4-methylpyridine In toluene at 60℃; for 1h; Inert atmosphere;
  • 63
  • [ 1450-75-5 ]
  • [ 109-94-4 ]
  • [ 51483-92-2 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere;
84% With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃;
81% With sodium hydride at 0 - 20℃; for 1.58333h; 1 Example 1: Preparation of a first intermediate 645mg 2-hydroxy-5-bromoacetophenone was added to the drying reaction bottle, 6ml of ethyl formate solution was added, the reaction system was cooled down to 0 °C, maintained at this temperature for 5 minutes; then 720mg of sodium hydride was added to the reaction system in four times within 2 hours, warmed to room temperature, after 30 minutes of the reaction, 1.3ml of methanol was quenched, Then 12.5ml of concentrated hydrochloric acid was added, stirred at room temperature overnight, after the end of the reaction, 10ml of ethyl acetate was dissolved, washed with 10ml of water, 10ml of saturated sodium bicarbonate, 10ml x 3 times of ethyl acetate for extraction, the resulting organic phase was combined and dried, and the solvent was removed under reduced pressure to obtain a crude product. By column chromatography to purify the crude product, the eluent in the column chromatography process is n-hexane and ethyl acetate in the ratio of 10:1 to obtain a 544mg first intermediate, with a yield of 81%.
Stage #1: 1-(5-bromo-2-hydroxyphenyl)ethan-1-one; ethyl formate With sodium hydride In tetrahydrofuran Reflux; Stage #2: With hydrogenchloride In methanol; water monomer at 20℃; for 14h;

  • 64
  • [ 51483-92-2 ]
  • [ 623-51-8 ]
  • C11H5BrO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 60℃; for 12h; Inert atmosphere;
  • 65
  • [ 51483-92-2 ]
  • [ 7284-07-3 ]
  • 6-((E)-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)vinyl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; Coupled Products 4a-d, 7b, 9, 11, 13, 15a-d, 17a,b, and 19a-d; Compound 4a; TypicalProcedure Jeffery General procedure: A mixture of compound 1a (150 mg, 0.5 mmol), 3 (93 mg, 0.5 mmol), TBAB (322 mg, 1mmol), K2CO3 (104 mg, 0.75 mmol), and Pd(OAc)2 (7 mg, 6 mol%) was stirred in anhydrousDMF (10 mL) at 100 °C for 3 h. Then the solvent was removed under reduced pressure andthe crude product was purified by silica gel (60-120 mesh) column chromatography usingHexane-EtOAc (1:2) as an eluent to give the solid compound 4a;
  • 66
  • [ 51483-92-2 ]
  • [ 1161723-18-7 ]
  • 6-((E)-2-((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-6-methoxy-3-(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-2-yl)vinyl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; silver nitrate In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere;
  • 67
  • [ 21665-16-7 ]
  • [ 51483-92-2 ]
  • 6-((Z)-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[2,3-d][1,3]dioxol-6(5H)-ylidene)methyl)-4H-chromen-4-one [ No CAS ]
  • 6-((E)-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[2,3-d][1,3]dioxol-6(5H)-ylidene)methyl)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 28% 2: 27% With potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; silver nitrate In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere; stereoselective reaction;
  • 68
  • [ 51483-92-2 ]
  • [ 100-63-0 ]
  • 6-bromo chromone phenylhydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In tetrahydrofuran; ethanol for 1h; Reflux; 2 Example 2:Synthesis of 2,6-bromochromone phenylhydrazone 2 mmol of phenylhydrazine was added to a flask containing 10 mL of tetrahydrofuran. The boiling water bath was stirred and dissolved until 20 mL of a solution of 2 mmol of 6-bromo-chromone in absolute ethanol was added dropwise. The mixture was refluxed for 1 h, 10 drops of hydrochloric acid, a pale yellow precipitate appears.Continuous boiling water bath reflux stirring 5h, stop water bath, add 20mL of distilled water, stirring, pale yellow precipitate color becomes dark, pumping filter was phenylhydrazone, yellow red needle-like product.Washed several times with anhydrous ether and dried in vacuo to give the product 6-bromochromone phenylhydrazone (4).
With hydrogenchloride In tetrahydrofuran; ethanol for 5h; Reflux; 2 Example 2: Synthesis of 6-bromochromone phenylhydrazone: 6-bromo-chromone and phenylhydrazine dehydration reaction of Schiff base method, the specific operation: take 2mmol of phenylhydrazine added to the flask containing 10mL of tetrahydrofuran, boiling water bath stirring to dissolve, and then slowly dropping 20mL dissolved 2mmol6-bromo-chromone anhydrous ethanol solution, continue boiling water bath reflux stirring 1h, dropping 10 drops of hydrochloric acid, a yellow precipitate appears.Continuous boiling water bath reflux stirring 5h, stop water bath, add 20mL of distilled water, stirring, pale yellow precipitate color becomes dark, pumping filter was phenylhydrazone, yellow red needle-like product.Washed several times with anhydrous ethyl ether, and dried in vacuo to give the product 6-bromochromone phenylhydrazone (4).
With hydrogenchloride In tetrahydrofuran for 6h; Reflux; 2 Example 2,6-bromo chromone phenylhydrazone Synthesis Take 2mmolPhenylhydrazineplusInto a flask containing 10 mL of tetrahydrofuran,Boiling water bath reflux to dissolve,And then slowly added 20 mL of an absolute ethanol solution containing 2 mmol of 6-bromochromone,Continue boiling water bath reflux stirring 1h,Dropping 10 drops of hydrochloric acid,A pale yellow precipitate appears.Continuous boiling water bath reflux stirring 5h,Stop the water bath,Add 20mL of distilled water to stir,Pale yellow precipitate darker,Smelting the phenylhydrazone,Yellow red needle products.Washed with anhydrous ether several times,Dried in vacuo to give the product 6-bromo ketone phenylhydrazone (4).
Stage #1: 6-bromo-1-benzopyran-4(4H)-one; phenylhydrazine In tetrahydrofuran; water for 1h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 5h; Reflux; 1.3 (3) Synthesis of 6-bromochromone phenylhydrazone Using 6-bromo chromone and phenylhydrazine dehydration reaction Schiff base method, the specific operation: Take 2mmol of phenylhydrazine was added to the flask containing 10mL of tetrahydrofuran,Boiling water bath was refluxed until dissolved,Then slowly added dropwise 20mL dissolved 2mmol 6-bromo chromone in absolute ethanol solution,Continue boiling water bath reflux stirring 1h, dropping 10 drops of hydrochloric acid, a pale yellow precipitate appears.Continuous boiling water bath reflux stirring 5h, stop the water bath, add 20mL distilled water, light yellow precipitate darker,Pumping was phenylhydrazone, yellow-red needle-shaped product. Rinse with anhydrous ether several times,The product was dried in vacuo to give 6-bromochromone phenylhydrazone (Compound 4).

  • 69
  • [ 51483-92-2 ]
  • [ 1589-82-8 ]
  • [ 1311265-05-0 ]
YieldReaction ConditionsOperation in experiment
30.5% Stage #1: 6-bromo-1-benzopyran-4(4H)-one With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Stage #2: phenylmagnesium bromide In tetrahydrofuran; dichloromethane at -78℃; for 1h; 31 2-Benzyl-6-bromochroman-4-one: To a solution of 6-bromo-4H-chromen-4-one (200 mg,0.8 89 mmol) in CH2C12 (1 mL) was added trimethylsilyl trifluoromethane-sulfonate(0.209 mL, 1.155 mmol) at rt. After stirring for lh, tetrahydrofuran (7 mL) was added andthen cooled to -78 °C. To the mixture was added benzylmagnesium bromide (1.284 mL,1.155 mmol). After stirring for lh at -78 °C, 1M aqueous NH4C1 was added and it waswarmed to rt and stirred at rt for 2 h. It was then quenched with water. It was then extracted with ether. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOac/hexane to obtain 2-benzyl-6-bromochroman-4-one (0.86 g, 2.71 mmol, 30.5 % yield). ‘H NMR (400MHz, CDC13) ö 8.00 (d, J=2.4 Hz, 1H), 7.57 (dd, J=8.8, 2.7 Hz, 1H), 7.46 - 7.18 (m,4H), 6.95 - 6.83 (m, 1H), 4.78 -4.60 (m, 1H), 3.23 (dd, J14.1, 6.2 Hz, 1H), 3.06 (dd, J=13.9, 6.4 Hz, 1H), 2.73 - 2.66 (m, 2H).
  • 70
  • [ 51483-92-2 ]
  • [ 7422-78-8 ]
  • 2-(1-allyl-1H-pyrazol-3-yl)-4-bromophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% In dimethyl sulfoxide at 100℃;
50 mg In dimethyl sulfoxide at 100℃; for 36h; 2-(1-Allyl-1H-pyrazol-3-yl)-4-bromophenol (11) 6-Bromochromone 10 (0.20 g, 0.87 mmol) and allylhydrazine 9 (90 mg, 1.3 mmol) were dissolved in DMSO (5 mL). The mixture was stirred at 100 °C for 36 h, until the reaction was completed, and cooled to ambient temperature. The mixture was diluted with EtOAc (20 mL), washed with water and brine, and dried over anhydrous MgSO4. After the solvent was removed in vacuo, the residue was purified by column chromatography on deactivated silica gel, with hexane/EtOAc (20:1) as the eluent, to obtain the corresponding product 11 (50 mg, 21 %) as a white solid. 1H NMR (600 MHz, CDCl3) δ 4.76 (tt, J = 6.0, 1.2 Hz, 2H), 5.23-5.32 (m, 2H), 5.99-6.05 (m, 1H), 6.60 (d, J = 2.4 Hz, 1H), 6.90 (d, J = 9.0 Hz, 1H), 7.27 (dd, J = 8.4, 2.4 Hz, 1H), 7.44 (d, J = 2.4 Hz, 1H), 7.64 (d, J = 2.4 Hz, 1H), 10.83 (s, 1H); 13C NMR (150 MHz, CDCl3) δ 54.8, 102.7, 111.1, 118.7, 119.0, 119.5, 128.7, 130.4, 131.7, 132.1, 150.2, 155.0; HRMS (ESI): mass calcd for C12H11BrN2O[M + H]+, 278.0055; found, 278.0054.
  • 71
  • [ 51483-92-2 ]
  • [ 38445-24-8 ]
YieldReaction ConditionsOperation in experiment
45% With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;
  • 72
  • [ 67-56-1 ]
  • [ 51483-92-2 ]
  • 6-bromo-2-(hydroxymethyl)chroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With di-tert-butyl peroxide at 140℃; for 15h; Inert atmosphere; Sealed tube;
41% With di-tert-butyl peroxide at 150℃; for 15h; Inert atmosphere; Schlenk technique; Sealed tube; 11 Example 11 6-bromochromone 1k (0.2mmol), di-tert-butyl peroxide (DTBP, 0.6mmol), under nitrogen protectionMethanol (1 mL) was added to a Schlenk reaction tube and sealed.Heat to 150 ° C and the reaction time was 15 hours.After completion of the reaction, the solvent was removed under reduced pressure, and the title product was obtained by column chromatography. The yield of 6-bromochromone 1k was 75%, and the yield of 6-bromochromanone 2k was 41%.1H NMR (CDCl3, 400MHz): δ 7.97 (d, J = 2.5 Hz, 1H), 7.55 (d, J = 8.8, 2.5 Hz, 1H), 6.90 (d,J=8.8 Hz, 1H), 4.58-4.53 (m, 1H), 4.00-3.98 (m, 1H), 3.85-3.82 (m, 1H), 2.97-2.89 (m, 1H),2.66-2.61 (m, 1H), 2.77 (s, 1H).
  • 73
  • [ 115237-38-2 ]
  • [ 51483-92-2 ]
YieldReaction ConditionsOperation in experiment
96 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 90℃; for 0.166667h; Microwave irradiation; Experimental Procedure for the Preparation of4H-chromen-4-one (3a) Method-- General procedure: A mixture of 2-hydroxy acetophenone 1 (200 mg, 1.47 mmol) and DMF-DMA(0.96 ml, 1.47 mmol) were introduced into a 2-5 mL initiator reaction vial. Themixture was irradiated for 10 minutes at 100 ° C under MW. The reaction mixturewas cooled to room temperature then 50% T3P in EtOAC was added and thereaction mixture was irradiated for 10 min at 90 ° C under MW. TLC analysis (30%ethyl acetate/ pet ether) showed completion of the reaction. The crude product wasdiluted with EtoAc and wash with water, brine and dried over anhydrous Na2SO4.The crude product was purified by column chromatography on a silica gel columnusing an EtOAc-hexane mixture as the eluent gave the compound 3a (200 mg, 92%) as an off white solid.
With hydrogenchloride In dichloromethane; water for 1h; Reflux; Step 2: Preparation of 4H-chromen-4-one (2B): To anoven dried round bottom flask, (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (10.0 g, 53.0 mmol)was dissolved in dichloromethane (50.0 mL). To this,conc. HCl (50 mL) was added and the mixture wasrefluxed for 1 h. It was cooled to rt and poured into coldwater. The organic layer was separated and the aqueouslayer was extracted with dichloromethane (2 × 30 mL).The combined organic extract was washed with waterand brine and dried over anhydrous MgSO4. The solventwas evaporated and dried under vacuum to obtain 4Hchromen-4-one as red solid in 90% yield (6.8 g).
  • 74
  • [ 51483-92-2 ]
  • [ 630-19-3 ]
  • 6-bromo-2-(tert-butyl)chroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With di-tert-butyl peroxide; isopropyl alcohol at 120℃; for 15h; Inert atmosphere; Sealed tube;
94% With di-tert-butyl peroxide In isopropyl alcohol at 120℃; for 15h; Inert atmosphere; Schlenk technique; Sealed tube; 7 Example 7 Under the protection of nitrogen,6-bromochromone 2g (0.2mmol),Pentaldehyde 2a (0.6 mmol) di-tert-butyl peroxide (DTBP, 0.5 mmol),Isopropanol (1 mL) was added to the Schlenk reaction tube.seal. Heat to 120 ° C and the reaction time was 15 hours.After completion of the reaction, the solvent was removed under reduced pressure, and the title product was obtained.The conversion of ketone 2g is 100%.The yield of 2-tert-butyl-6-bromochromanone 3ga was 94%.
  • 75
  • [ 591-50-4 ]
  • [ 51483-92-2 ]
  • 6-bromo-3-(phenylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With copper(l) iodide; sulfur In N,N-dimethyl-formamide at 135℃; for 24h; Sealed tube;
  • 76
  • [ 51483-92-2 ]
  • [ 74-88-4 ]
  • 6-bromo-3-(methylthio)-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With copper(l) iodide; sodium thiosulfate In N,N-dimethyl-formamide at 135℃; for 24h; Sealed tube;
  • 77
  • [ 51483-92-2 ]
  • copper(l) cyanide [ No CAS ]
  • [ 55168-34-8 ]
YieldReaction ConditionsOperation in experiment
85% In 1-methyl-pyrrolidin-2-one at 200℃; for 3h; 37.A Step A: 4-oxo-4H-chromene-6-carhonitrile Copper(T) cyanide (88 mg. 0.978 mmol) was added to 6-bromo-4H-chromen-4-one (200 mg, 0.889 mmol) in NM1 (3.0 ml). The reaction mixture was heated to 200 0Q for 3 hr. Reaction mixture was cooled and saturated ammonium chloride was added. Aqueous layer was extracted with ethylacetate, washed with brine, dried with anhydrous sodium sulfate and evaporated to give crude which was purified by combiflash to afford 4-oxo-4H-chromene-6-carbonitrile (130 mg, 0760 mrnoi, 85 % ) as brown color solid.
  • 78
  • [ 51483-92-2 ]
  • [ 556-82-1 ]
  • 6-bromo-2-(4-hydroxy-2-methylbutan-2-yl)-2,3-dihydrochromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With phenylsilane; iron(III) acetylacetonate In ethanol at 40℃; for 5h;
  • 79
  • [ 51483-92-2 ]
  • [ 100-63-0 ]
  • [ 1360445-05-1 ]
YieldReaction ConditionsOperation in experiment
15% In dimethyl sulfoxide at 100℃; 4-Bromo-2-(1-phenyl-1H-pyrazol-3-yl)phenol(11b) 6-bromochromone (300 mg, 1.31mmol) andphenylhydrazine(160.6 mg, 1.44 mmol) were dissolved in DMSO (5 mL). The mixture was stirred at 100°C. Until the reaction was completed, and cooled to ambient temperature. The mixture was diluted with EtOAc, washed with water and brine and the combined organic layer dried over anhydrous MgSO4, concentrated under reduced pressure.The residue was purified by flash column chromatography on silica gel (ethyl acetate/hexanes = 1: 10) to afford11b(22 mg, 15%).1H NMR (600 MHz, CDCl3) δ 10.84 (s, 1H), 7.98 (d,J= 2.6 Hz, 1H), 7.71 (d,J= 2.4 Hz, 1H), 7.68 - 7.66 (m, 2H),7.51 - 7.48 (m, 2H), 7.36 - 7.32 (m, 2H), 6.95 (d,J= 8.7 Hz, 1H), 6.83 (d,J= 2.6 Hz, 1H).13C NMR (151 MHz, CDCl3) δ 155.2, 151.7, 139.2, 132.3, 129.8, 129.1, 128.2, 127.2, 119.2, 119.1, 118.2, 111.3, 104.8.HRMS (EI): mass calculated for C15H11BrN2O [M+], 314.0055; found,314.0058.
  • 80
  • [ 51483-92-2 ]
  • [ 555-96-4 ]
  • 2-(1-benzyl-1H-pyrazol-3-yl)-4-bromophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% In ethanol at 100℃; 2-(1-Benzyl-1H-pyrazol-3-yl)-4-bromophenol (11c) 6-bromochromone (430 mg, 1.91mmol) andbenzylhydrazine(510 mg, 3.2 mmol) were dissolved inEtOH(5 mL). The mixture was stirred overnight at 100°C. Until the reaction was completed, and cooled to ambient temperature. The mixture was diluted with EtOAc, washed with water and brine and the combined organic layer dried over anhydrous MgSO4, concentrated under reduced pressure.The residue was purified by flash column chromatography on silica gel (ethyl acetate/hexanes = 1: 10) to afford11c(300 mg, 48%).1H NMR (600 MHz, CDCl3) δ 10.86 (s, 1H), 7.66 (d,J= 2.4 Hz, 1H), 7.42 (d,J= 2.5 Hz, 1H), 7.38 - 7.32 (m, 3H), 7.28 (dd,J= 8.7, 2.4 Hz, 1H), 7.25 - 7.23 (m, 2H), 6.91 (d,J= 8.7 Hz, 1H), 6.60 (d,J= 2.5 Hz, 1H), 5.30 (s, 2H).13C NMR (150 MHz, CDCl3) δ 154.9, 150.3, 135.6, 131.7, 130.7, 129.0, 128.7, 128.5, 127.8, 118.9, 118.7, 111.1, 102.9, 56.2.HRMS (EI): mass calculated for C16H13BrN2O [M+], 328.0211; found,328.0208.
  • 81
  • [ 51483-92-2 ]
  • 6-bromo-3-hydroxy-4H-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% Stage #1: 6-bromo-1-benzopyran-4(4H)-one With dihydrogen peroxide; sodium hydroxide In dichloromethane at 0℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride at 70℃; for 1h; Inert atmosphere;
Stage #1: 6-bromo-1-benzopyran-4(4H)-one With dihydrogen peroxide; sodium hydroxide In dichloromethane at 0 - 15℃; Stage #2: With hydrogenchloride In water at 70℃; for 1h; Step 3: Preparation of 3-hydroxychromone (3B): To anoven dried round bottom flask 4H-chromen-4-one (5.0 g,34.2 mmol) was dissolved in dichloromethane (50 mL).Sodium hydroxide (2.0 g, 51.3 mmol) was added to it.Reaction mixture was cooled to 0 °C and H2O2 (30%w/v, 13.5 mL, 119.7 mmol) was slowly added at thesame temperature. After complete addition, the mixturewas stirred at 0-15 °C. After complete disappearance ofchromone as monitored by TLC, it was quenched withwater and extracted with dichloromethane (3 × 20 mL).The combined organic extract was washed with waterand brine, dried over anhydrous MgSO4 and evaporatedusing rotatory evaporator. In the second step, conc. HCl(50 mL) was added to the crude reaction mixture and wasstirred at 70 °C for 1 h. After that, it was cooled to rt andpoured into water. The solid precipitate obtained was filteredand washed with water and dried under vacuum toobtain a white solid as 3-hydroxychromone in 64% yield(3.54 g).
Multi-step reaction with 2 steps 1: sodium hydroxide; dihydrogen peroxide / dichloromethane; water / 48 h / 0 - 20 °C 2: hydrogenchloride / 2 h / 70 °C
  • 82
  • [ 51483-92-2 ]
  • [ 1666-13-3 ]
  • C15H9BrO2Se [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tert.-butylhydroperoxide; N-iodo-succinimide In water; N,N-dimethyl-formamide at 70℃; for 3h; regioselective reaction;
  • 83
  • [ 72757-63-2 ]
  • [ 51483-92-2 ]
  • (R)-2-[(R)-2-allyl-5-oxo-2H-fur-2-yl]-6-bromo-4-chromanone [ No CAS ]
  • C16H13BrO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With diethylzinc; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere; Overall yield = 72 %; Overall yield = 50.2 mg; stereoselective reaction;
  • 84
  • [ 51483-92-2 ]
  • 2-(4-(5-oxo-2,5-dihydrofuran-2-yl)butyl)isoindoline-1,3-dione [ No CAS ]
  • 2-(4-{(R)-2-[(R)-6-bromo-4-oxo-2-chromanyl]-5-oxo-2H-fur-2-yl}butyl)-1,3-isoindolinedione [ No CAS ]
  • C25H20BrNO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With diethylzinc; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere; stereoselective reaction;
Same Skeleton Products
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