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3,5-Dichloropyridine Basic information Product Name: 3,5-Dichloropyridine Synonyms: 3,5-dichloro-pyridin;3,5-Dichloroypyridine;3,5-DICHLOROPYRIDINE;Dichloropyridine,98%;3,5-Dichloripyridine;3,5-CHLOROPYRIDINE;3,5-Dichloropyridine,97%;3.5-Dichl
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3,5-dicholoropyridine N-oxide
3,5-dichloropyridine
Conditions | Yield |
---|---|
With 2,3-dimethyl-2,3-butane diol; bis(N,N-dimethylformamide)dichloridodioxidomolybdenum(VI) In N,N-dimethyl acetamide at 130℃; Microwave irradiation; Sealed tube; Green chemistry; chemoselective reaction; | 95% |
2,3,5-trichloropyridine
3,5-dichloropyridine
Conditions | Yield |
---|---|
With acetic acid; zinc In water at 65 - 95℃; for 1 - 5.25h; Product distribution / selectivity; | 87.3% |
lithioacetonitrile
3,5-dichloropyridine-4-carbonitrile
A
3,5-dichloropyridine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.0833333h; | A n/a B 73% |
Conditions | Yield |
---|---|
With sodium acetate; acetic acid; zinc at 100℃; for 5.5h; Product distribution / selectivity; | 65% |
With acetic acid; zinc In water at 81 - 82℃; for 30h; Product distribution / selectivity; | 44.6 %Chromat. |
With acetic acid; zinc In 1,4-dioxane; water at 81 - 82℃; for 29h; Product distribution / selectivity; | 60.8 %Chromat. |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
A
3,5-dichloropyridine
B
etoricoxib
Conditions | Yield |
---|---|
With ammonium acetate In propionic acid at 125℃; | A n/a B 62% C 15% |
methyllithium
3,5-dichloropyridine-4-carbonitrile
A
3,5-dichloro-4-picoline
B
3,5-dichloropyridine
D
methyl 3,5-dichloro-4-pyridyl imine
Conditions | Yield |
---|---|
In tetrahydrofuran at -75℃; for 0.333333h; | A 12% B 12% C 9% D 57% |
methyllithium
3,5-dichloropyridine-4-carbonitrile
A
3,5-dichloro-4-picoline
B
3,5-dichloropyridine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.333333h; | A 3% B 45% C 32% |
2,3,5-trichloropyridine
A
3,5-dichloropyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In dimethyl sulfoxide Heating; | A 18% B 28% |
Conditions | Yield |
---|---|
With phosphorus pentachloride |
2-methoxy-3,4-dihydro-2H-pyran
A
3-Chloropyridine
B
3,5-dichloropyridine
Conditions | Yield |
---|---|
With chlorine Eintragen des Reaktionsgemisches in eine heisse wss. Loesung von Ammoniumchlorid und Eisen(III)-chlorid; | |
With chlorine Eintragen des Reaktionsgemisches in eine heisse wss. Loesung von Ammoniumchlorid und Eisen(III)-chlorid; |
5-chloropyridin-3-amine
3,5-dichloropyridine
3,5-dichloropyridine-2-carboxylic acid
3,5-dichloropyridine
Conditions | Yield |
---|---|
Erhitzen auf Temperaturen oberhalb des Schmelzpunkts; |
3,5-dichloropyridine-4-carboxylic acid
3,5-dichloropyridine
Conditions | Yield |
---|---|
at 230℃; im Rohr; |
Conditions | Yield |
---|---|
With chlorine at 115 - 120℃; |
Conditions | Yield |
---|---|
With chlorine at 170℃; | |
With chlorine at 200℃; |
nopinone
A
5-chloropyrimidine
B
3,5-dichloropyridine
C
5-Chloro-10,10-dimethyl-3-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene
Conditions | Yield |
---|---|
Multistep reaction. Yields of byproduct given; | |
Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With 4-bromoanisole cation radical In acetonitrile at 23℃; Rate constant; Mechanism; |
N-methyl-3,5-dichloropyridinium iodide
triphenylphosphine
A
3,5-dichloropyridine
B
methyl-triphenylphosphonium iodide
Conditions | Yield |
---|---|
In acetonitrile at 115℃; Rate constant; Thermodynamic data; k2=15.1s-1M-1; var. temp. ΔS*=9.1 e.u. ΔH*=29.7kcal/mol; |
N-methyl-3,5-dichloropyridinium iodide
methyl iodide
3,5-dichloropyridine
Conditions | Yield |
---|---|
In acetonitrile at 25℃; Kinetics; Equilibrium constant; Thermodynamic data; ΔG(excit.), ΔH(excit.), ΔS(excit.); |
3,5-dichloropyridine
Conditions | Yield |
---|---|
With glycerol beim Destillieren; |
Conditions | Yield |
---|---|
With phosphorus pentachloride at 200℃; |
pyridine
chlorine
A
3,4,5-trichloropyridine
B
3,5-dichloropyridine
Conditions | Yield |
---|---|
at 220℃; |
pyridine
chlorine
A
3-Chloropyridine
B
3,4,5-trichloropyridine
C
2,3,4,5,6-pentachloropyridine
D
3,5-dichloropyridine
Conditions | Yield |
---|---|
at 170℃; beim Behandeln des Pyridin-hydrochlorids; |
3,4,5-trichloropicolinic acid
hydrogen iodide
A
3,5-dichloropyridine-2-carboxylic acid
B
3,5-dichloropyridine
3,5-dichloropyridine-4-carboxaldehyde
3,5-dichloropyridine
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloropyridine-4-carboxaldehyde With phenyllithium In diethyl ether; hexane at -75℃; for 2h; Stage #2: With hydroxide In water |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 180 - 220 °C / im Rohr und Zersetzen des Reaktionsprodukts mit Wasser 2: 230 °C / im Rohr View Scheme |
3,5-dichloro-4-hydroxy-pyridine-2-carboxylic acid
3,5-dichloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: POCl3; PCl5 3: ethanolic alkaline solution 4: aqueous HI; red phosphorus 5: Erhitzen auf Temperaturen oberhalb des Schmelzpunkts View Scheme |
3,5-dichloropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: ethanolic alkaline solution 3: aqueous HI; red phosphorus 4: Erhitzen auf Temperaturen oberhalb des Schmelzpunkts View Scheme |
Conditions | Yield |
---|---|
at 100℃; under 4500360 Torr; for 72h; | 100% |
3,5-dichloropyridine
allyl alcohol
3-chloro-5-propen-cis-yloxypyridine
Conditions | Yield |
---|---|
Stage #1: allyl alcohol With sodium at 80℃; for 3h; Stage #2: 3,5-dichloropyridine In dimethyl sulfoxide at 60℃; for 1h; | 100% |
Conditions | Yield |
---|---|
Stage #1: butan-1-ol With sodium at 80℃; for 3h; Stage #2: 3,5-dichloropyridine In dimethyl sulfoxide at 70℃; for 10h; | 100% |
3,5-dichloropyridine
Dimethylphenylsilane
3,5-dichloro-1-[dimethyl(phenyl)silyl]-1,4-dihydropyridine
Conditions | Yield |
---|---|
With C29H38PRuS(1+)*C32H12BF24(1-) In neat (no solvent) at 20℃; for 12h; Inert atmosphere; Glovebox; | 98% |
With tris(pentafluorophenyl)borate In (2)H8-toluene at 85℃; for 5h; Inert atmosphere; chemoselective reaction; | 92 %Spectr. |
3,5-dichloropyridine
3,5-dicholoropyridine N-oxide
Conditions | Yield |
---|---|
With peracetic acid In chloroform; acetic acid at 50℃; for 67h; | 96% |
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 24℃; for 17h; | 94% |
With bis-trimethylsilanyl peroxide; per-rhenic acid In dichloromethane; water at 24℃; for 20h; | 90% |
3,5-dichloropyridine
sodium thiomethoxide
5-Chloro-3-methylsulfenylpyridine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Heating; | 95% |
In N,N-dimethyl-formamide at 20℃; for 1h; |
3,5-dichloropyridine
5-Chloro-3-methylsulfenylpyridine
Conditions | Yield |
---|---|
With mesna In N,N-dimethyl-formamide Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide; polyaniline-supported palladium In water at 100℃; for 6h; Suzuki coupling; | 95% |
With caesium carbonate; dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-) In 1,2-dimethoxyethane Suzuki-Miyaura cross-coupling; Heating; | 74% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloropyridine; benzaldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With methanol; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; | 94% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloropyridine; pivalaldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With methanol; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; | 94% |
Conditions | Yield |
---|---|
With sodium t-butanolate; XPhos; palladium diacetate In toluene; tert-butyl alcohol at 120℃; for 14h; Buchwald-Hartwig amination; | 93% |
tetrafluoroboric acid diethyl ether
3,5-dichloropyridine
Conditions | Yield |
---|---|
In diethyl ether at 0 - 20℃; | 93% |
3,5-dichloropyridine
tert-butyl 1,4-diazepine-1-carboxylate
4-(5-chloropyridin-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; XPhos In toluene; tert-butyl alcohol at 120℃; for 18h; Buchwald-Hartwig reaction; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 90℃; for 2h; ethoxylation; | 91% |
89% | |
In dimethyl sulfoxide at 80℃; for 1h; |
pyridine-4-carbonitrile
3,5-dichloropyridine
[4-(3,5-dichloro)pyridyl](4-pyridyl)ketimine
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; | 91% |
3,5-dichloropyridine
3,5-dichloropyridine-4-carboxaldehyde
bis[4-(3,5-dichloro)pyridyl]methanol
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; | 91% |
Methyl formate
3,5-dichloropyridine
3,5-dichloropyridine-4-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Methyl formate In tetrahydrofuran at -78℃; for 1.4h; Further stages.; | 90% |
3,5-dichloropyridine
acetaldehyde
1-(3,5-dichloropyridin-4-yl)ethan-1-ol
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloropyridine With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexanes at -78℃; Stage #2: acetaldehyde In tetrahydrofuran; hexanes at -78℃; for 3h; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes at -78℃; | 90% |
Stage #1: 3,5-dichloropyridine; acetaldehyde With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78℃; for 3h; Stage #2: With ammonium chloride In tetrahydrofuran; hexane; water at -78 - 20℃; | 90% |
With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78℃; | 90% |
Stage #1: 3,5-dichloropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: acetaldehyde In tetrahydrofuran at 20℃; for 2h; | 66% |
With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 3h; | 65% |
Conditions | Yield |
---|---|
With copper(l) iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 90% |
3,5-dichloropyridine
p-tolylboronic pinacol ester
3,5-bis(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium hydroxide In neat (no solvent) at 110℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With C14H22N2P(1+)*CF3O3S(1-) In [D3]acetonitrile at 28℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction; | 89% |
3,5-dichloropyridine
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloropyridine With Bu3MgLi In tetrahydrofuran at -10℃; for 2h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 18h; Further stages.; | 88% |
Stage #1: 3,5-dichloropyridine With lithium diisopropyl amide In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; | 44% |
Multi-step reaction with 2 steps 1.1: Bu3MgLi / tetrahydrofuran / 2 h / -10 °C 1.2: D2O / tetrahydrofuran 2.1: I2 / tetrahydrofuran; H2O View Scheme |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; | 87% |
In dimethyl sulfoxide at 70℃; for 2h; | 77% |
In dimethyl sulfoxide at 80℃; for 1h; | 62% |
3,5-dichloropyridine
sodium isopropanethiolate
3,5-bis(isopropylthio)pyridine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; | 87% |
3,5-dichloropyridine
5-chloro-2-methoxypyridine
Conditions | Yield |
---|---|
With sodium methylate In N,N-dimethyl-formamide at 80℃; for 2h; | 87% |
3,5-dichloropyridine
3,5-bis(isopropylthio)pyridine
Conditions | Yield |
---|---|
With sodium isopropanethiolate In N,N-dimethyl-formamide at 80℃; for 15h; | 87% |
1-bromo-4-methoxy-benzene
3,5-dichloropyridine
3,5-bis-(4-methoxyphenyl)-pyridine
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-methoxy-benzene With magnesium In tetrahydrofuran Metallation; Stage #2: 3,5-dichloropyridine With dibromobis(triphenylphosphine)nickel(II) In tetrahydrofuran Grignard reaction; Further stages.; | 86% |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); magnesium; ethylene dibromide In tetrahydrofuran at 0℃; Inert atmosphere; Reflux; | 73% |
3,5-dichloropyridine
4-bromo-3,5-dichloropyridine
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloropyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75℃; for 2h; Stage #2: With bromine In tetrahydrofuran; hexane at -75℃; for 3h; | 86% |
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