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inquiry2-thioxobenzo[d][1,3]dioxole-5-carbaldehyde
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
Conditions | Yield |
---|---|
With bromine trifluoride In CFCl3; chloroform at 0℃; for 0.0166667h; | 95% |
5-dichloromethyl-2,2-difluorobenzo-(1,3)-dioxole
hexamethylenetetramine
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride In water |
5-bromo-2,2-difluoro-2H-1,3-benzodioxole
N,N-dimethyl-formamide
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2,2-difluoro-2H-1,3-benzodioxole With n-butyllithium In tetrahydrofuran for 0.166667h; Cooling with acetone-dry ice; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 2h; Cooling with acetone-dry ice; Stage #3: With water; ammonium chloride In tetrahydrofuran | |
Stage #1: 5-bromo-2,2-difluoro-2H-1,3-benzodioxole With isopropylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 5h; Inert atmosphere; Large scale; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -25℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Large scale; | 28.6 g |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / water / 2 h / 0 °C 2: bromine trifluoride / CFCl3; chloroform / 0.02 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: iron; bromine / 20 - 30 °C / Inert atmosphere; Large scale 2.1: isopropylmagnesium chloride / tetrahydrofuran / 5 h / -10 - 0 °C / Inert atmosphere; Large scale 2.2: 2 h / -25 °C / Inert atmosphere; Large scale View Scheme |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
1-t-Butoxycarbonylpiperazine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 0 - 20℃; | 99% |
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 16h; |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
(S)-2-methylpropane-2-sulfinamide
Conditions | Yield |
---|---|
With copper(II) sulfate In dichloromethane at 18 - 25℃; for 16h; Inert atmosphere; | 95% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
toluene-4-sulfonic acid hydrazide
Conditions | Yield |
---|---|
In ethanol Reflux; | 88% |
In methanol at 20℃; for 12h; Inert atmosphere; Sealed tube; |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
Methyltriphenylphosphonium bromide
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 0 - 25℃; for 48h; Schlenk technique; Inert atmosphere; | 85% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | 80% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 76% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere; | 50% |
Conditions | Yield |
---|---|
With triethylsilane; palladium on carbon; TPGS-750-M In water at 45℃; for 4h; | 85% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
methylmagnesium bromide
1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)ethan-1-ol
Conditions | Yield |
---|---|
Stage #1: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde; methylmagnesium bromide In diethyl ether at 0 - 20℃; for 0.25 - 0.333333h; Stage #2: With water at 0℃; | 83.5% |
piperazine
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
1-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)piperazine
Conditions | Yield |
---|---|
With hydrogen; 20% palladium hydroxide-activated charcoal In methanol; toluene at 20 - 70℃; under 760.051 Torr; for 36h; | 83% |
Stage #1: piperazine; 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In methanol at 20℃; for 18h; Stage #2: With 20% palladium hydroxide on charcoal; hydrogen In methanol at 70℃; under 760.051 Torr; | 83% |
Stage #1: piperazine; 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In methanol at 20℃; for 18h; Inert atmosphere; Stage #2: With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol at 70℃; under 760.051 Torr; | 83% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
cyclohexylamine
N-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]cyclohexanamine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 25℃; Molecular sieve; | 82% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid hydrazide
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 82% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde; (1S,3S,4R)-4-[(3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methylidene-octahydro-1H-inden-5-yl]-3-(hydroxymethyl)-4-methylcyclohexan-1-ol In methanol for 0.5h; Reflux; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate at 20℃; Inert atmosphere; | 81% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
Conditions | Yield |
---|---|
With eosin Y disodium salt In acetonitrile at 80℃; for 48h; Smiles Aromatic Rearrangement; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; diastereoselective reaction; | 80% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
(2,2-difluoro-1,3-benzodioxol-5-yl)methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20 - 30℃; for 3.5h; Reagent/catalyst; Inert atmosphere; Large scale; | 77.7% |
With methanol; sodium tetrahydroborate |
tetrahydrofuran-2,4-dione
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
1,10-phenanthroline-5-amine
Conditions | Yield |
---|---|
In ethanol Reflux; | 77% |
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine; (1,2,3,4,5-pentamethylcyclopentadienyl)(tetrahydrofuran)dicarbonyliron(II) tetrafluoroborate; boron trifluoride diethyl etherate In toluene at 100℃; for 24h; | 76% |
4-hydroxy-2(5H)-furanone
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
9-(2,2-difluoro-1,3-benzodioxol-5-yl)-6,9-dihydro[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one
Conditions | Yield |
---|---|
Inert atmosphere; Reflux; | 75% |
Conditions | Yield |
---|---|
Stage #1: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde With zinc(II) iodide In dichloromethane at 10 - 15℃; Stage #2: trimethylsilyl cyanide In dichloromethane at 20℃; for 1h; | 75% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
1,10-phenanthroline-5,6-dione
2-(3',3'-difluoro-3,4-methylenedioxyphenyl)imidazo[4,5-f][1,10]phenanthroline
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 2h; Reflux; | 74% |
With ammonium acetate; acetic acid for 2h; Reflux; | 74% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
[1-(6-ethyl-4,4-dimethyI-1,2,3,4-tetrahydro-quinolin-7-yl)-ethyl]-carbamic acid tert-butyl ester
{1-[1-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-6-ethyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl]-ethyl}-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With sodium cyanoborohydride In tetrahydrofuran at 65℃; for 20h; sealed tube; | 74% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
3,4-(difluoromethylenedioxy)-6-nitrobenzaldehyde
Conditions | Yield |
---|---|
With nitric acid; trifluoroacetic acid In dichloromethane at -60 - 4℃; Nitration; | 73% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
(2,2-difluorobenzo-1,3-dioxol-5-yl)methyl 2,2-difluorobenzo-1,3-dioxole-5-carboxylate
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate; cyclohexyldiphenylphosphine In 1,4-dioxane at 80℃; for 20h; Tishchenko reaction; Inert atmosphere; | 73% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
1-(2,2-difluorobenzo[1,3]dioxan-5-yl)ethanone oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 6h; | 72% |
pyrrolidine
4-hydroxy[1]benzopyran-2-one
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; | 71% |
Conditions | Yield |
---|---|
With chromium chloride; (±)N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II); phenylsilane; 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate In tetrahydrofuran; acetonitrile at 22℃; for 24h; Inert atmosphere; chemoselective reaction; | 71% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
malonic acid
3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-acrylic acid
Conditions | Yield |
---|---|
With piperidine; pyridine for 3h; Heating / reflux; | 70% |
With piperidine In pyridine for 3h; Heating / reflux; | 70% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
malonic acid
3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-acrylic acid
Conditions | Yield |
---|---|
With pyridine; piperidine for 3h; Knoevenagel Condensation; Heating / reflux; | 70% |
Conditions | Yield |
---|---|
With acetylacetonatodicarbonylrhodium(l); potassium formate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 130℃; for 16h; Inert atmosphere; Sealed tube; | 66% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 64% |
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde
2-[(2-carboxyacetyl)amino]benzoic acid
Conditions | Yield |
---|---|
With piperidine In toluene for 0.5h; Knoevenagel Condensation; Dean-Stark; Reflux; | 62% |
Conditions | Yield |
---|---|
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; Inert atmosphere; | 62% |
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