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2,2-dimethylpropane
A
3,3-dimethylpyrrolidine-2,5-dione
B
bromodichloromethane
C
2,2-dimethylpropyl bromide
D
3-bromo-3-methylbutanoyl isocyanate
Conditions | Yield |
---|---|
With ethene; dichloromethane; 22DMNBS; bromine at 12℃; for 30h; Irradiation; Further byproducts given. Yields of byproduct given; | A 67.7% B 32.3% C 45.2% D n/a |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium bromide; 18-crown-6 ether In water at 0℃; for 48h; | 38% |
With aluminium trichloride; hydrogen bromide | |
With aluminum tri-bromide; hydrogen bromide | |
With hydrogen bromide; aluminium |
Conditions | Yield |
---|---|
With aluminium trichloride at 20 - 25℃; |
methane
bromodichloromethane
Conditions | Yield |
---|---|
With sulfur trioxide; sodium bromide; sodium chloride at 600 - 700℃; |
Conditions | Yield |
---|---|
With bromine at 220℃; | |
With N-Bromosuccinimide; bromine at 14 - 15℃; | 0.50 mmol |
With N-Bromosuccinimide at 15℃; Irradiation; competitive brominaton reactions with neopentane; further brominating systems (NBS-Br2; NBS-DCE); |
Conditions | Yield |
---|---|
With aluminium trichloride | |
at 135℃; | |
With sodium hydroxide In various solvent(s) Mechanism; Ambient temperature; effects of additives: p-dinitrobenzene and di-tert-butyl nitroxide; | |
With aluminium trichloride beim Erhitzen auf Siedetemperatur; | |
at 135℃; unter CO2-Druck; |
2-bromo-2,2-dichloro-ethane-1,1-diol
bromodichloromethane
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With hypobromite |
2,2-dimethylpropane
2,2-dimethyl-N-bromosuccinimide
A
3,3-dimethylpyrrolidine-2,5-dione
B
bromodichloromethane
C
2,2-dimethylpropyl bromide
D
3-bromo-3-methylbutanoyl isocyanate
Conditions | Yield |
---|---|
With ethene; dichloromethane; bromine at 12℃; for 0.333333h; Irradiation; various molar ratios of educts; neopentane/methylene chloride competition with 2,2-dimethylsuccinimidyl radical; mechanism; |
Conditions | Yield |
---|---|
With N-Bromosuccinimide at 15℃; Irradiation; competition reaction with neopentane; relative rate constants for mediated brominations; additives - Br2, BrCCl3, CH2CCl2; |
Conditions | Yield |
---|---|
With acetyl hypobromite; bromine In dichloromethane at -78℃; for 3h; Product distribution; Mechanism; Irradiation; other substrates; | |
With acetyl hypobromite; bromine In dichloromethane at -78℃; for 3h; Irradiation; |
ethene
dichloromethane
methylcyclopropane
2,2-dimethyl-N-bromoglutarimide
A
1-bromo-4-butene
B
2,2-dimethylglutarimide
C
bromodichloromethane
E
ethylene dibromide
F
cyclopropylcarbinyl bromide
Conditions | Yield |
---|---|
at 15℃; for 1h; Product distribution; Kinetics; Mechanism; Irradiation; | A 1.7 % Chromat. B 50.4 % Chromat. C 12.8 % Chromat. D 50.1 % Chromat. E 2.0 % Chromat. F 18.0 % Chromat. |
dichloromethane
methylcyclopropane
2,2-dimethyl-N-bromoglutarimide
A
1-bromo-4-butene
B
2,2-dimethylglutarimide
C
bromodichloromethane
D
1,3-dibromobutane
E
cyclopropylcarbinyl bromide
Conditions | Yield |
---|---|
at 15℃; for 1h; Product distribution; Mechanism; Kinetics; Irradiation; | A 3.2 % Chromat. B 95.9 % Chromat. C 24.1 % Chromat. D 8.5 % Chromat. E 34.5 % Chromat. |
Conditions | Yield |
---|---|
With bromine; chlorine In trichlorofluoromethane at 10℃; for 0.0166667h; Irradiation; Yield given; |
Conditions | Yield |
---|---|
With ethyl bromide; aluminum oxide; tetrabutyl phosphonium bromide at 170℃; | A 9.5 % Spectr. B 0.5 % Spectr. |
chloroform
A
bromodichloromethane
B
chlorodibromomethane
C
Bromoform
Conditions | Yield |
---|---|
With carbon tetrabromide; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Mechanism; Ambient temperature; var. reag.: CBrCl3; equilibrium; products determined by GC-MS; |
Bromoform
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
Conditions | Yield |
---|---|
With dichloromethane; aluminum oxide; tetrabutyl phosphonium bromide at 170℃; | A 7 % Spectr. B 1 % Spectr. C 28 % Spectr. |
With tetrachloromethane; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Mechanism; Ambient temperature; var.reag.: fluorotrichloromethane; equilibrium; products determined by GC-MS; |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium chloride; N-benzyl-N,N,N-triethylammonium chloride In water Heating; Yield given. Yields of byproduct given; |
Bromotrichloromethane
A
bromodichloromethane
B
chloroform
C
hexachloroethane
Conditions | Yield |
---|---|
With perchloric acid; CoW7-; sodium perchlorate In water; acetonitrile at 20℃; Rate constant; Product distribution; pH 7; reaction with Co(II)sepuchrate2- at 50 deg C; electron transfer reactions of polyhaloalkanes with Co(II)W12O407- and Co(II)sepulchrate2+, order of reactivity toward Co(II)W12O407-, trapping experiments with N-t-butyl-α-phenylnitrone; | A n/a B 72 % Spectr. C 2 % Spectr. |
ethene
dichloromethane
2,2-dimethyl-N-bromoglutarimide
cyclopropane
A
2,2-dimethylglutarimide
B
bromodichloromethane
C
cyclopropyl bromide
Conditions | Yield |
---|---|
Product distribution; Mechanism; Kinetics; Irradiation; | A n/a B 24 % Chromat. C 22 % Chromat. D 40 % Chromat. |
dichloromethane
cyclopropane
A
bromodichloromethane
B
cyclopropyl bromide
Conditions | Yield |
---|---|
With 2,2-dimethyl-N-bromoglutarimide Product distribution; Mechanism; Irradiation; | A 42 % Chromat. B 53 % Chromat. |
DL-methionine sulfone
chloride
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
dichloroacetonitrile
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In phosphate buffer sulfo-haloform reaction; Enzymatic reaction; |
chloride
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
1,1-Dichloroacetone
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In phosphate buffer haloform reaction; Enzymatic reaction; Further byproducts given; |
chloro bromomethyl
bromodichloromethane
Conditions | Yield |
---|---|
With chlorine at 74.85 - 554.85℃; Rate constant; Kinetics; |
orcinol
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
Bromoform
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hypobromide for 1h; pH=8; Product distribution; Oxidation; halogenation; |
p-cresol
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
Bromoform
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hypobromide for 1h; pH=8; Product distribution; Oxidation; halogenation; |
3,4-Dihydroxybenzoic acid
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
Bromoform
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hypobromide for 1h; pH=8; Product distribution; Oxidation; halogenation; |
4-methyl resorcinol
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
Bromoform
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hypobromide for 1h; pH=8; Product distribution; Oxidation; halogenation; |
4-hydroxysalicylic acid
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
Bromoform
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hypobromide for 1h; pH=8; Product distribution; Oxidation; halogenation; |
2-methylbenzene-1,4-diol
A
bromodichloromethane
B
chloroform
C
chlorodibromomethane
D
Bromoform
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hypobromide for 1h; pH=8; Product distribution; Oxidation; halogenation; |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Schlenk technique; Inert atmosphere; Sealed tube; Large scale; | 96% |
N-methyl-3-phenylindole
bromodichloromethane
1-methyl-3-phenyl-1H-indole-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: N-methyl-3-phenylindole; bromodichloromethane With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane at 30℃; | 95% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 94% |
Conditions | Yield |
---|---|
Stage #1: bromodichloromethane; 1-ethyl-3-phenyl-1H-indole With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane at 30℃; | 93% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 93% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 93% |
bromodichloromethane
(8R,9S,13S,14S)-13-methyl-3-vinyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[α]phenanthren-17-one
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 92% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 91% |
Conditions | Yield |
---|---|
Stage #1: 4-Methoxystyrene; bromodichloromethane With N,N,N',N'',N'''-pentamethyldiethylenetriamine; water; copper hydroxide; sodium iodide In acetonitrile at 40℃; for 24h; Inert atmosphere; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate Catalytic behavior; Solvent; Reagent/catalyst; | A 9 %Spectr. B 90% |
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper hydroxide; potassium iodide In acetonitrile at 40℃; for 24h; Reagent/catalyst; Inert atmosphere; | A 31 %Spectr. B 2 %Spectr. |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 90% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 88% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 80℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 88% |
1-ethenyl-4-methylbenzene
bromodichloromethane
3-(4-methylphenyl)acrylaldehyde
Conditions | Yield |
---|---|
Stage #1: 1-ethenyl-4-methylbenzene; bromodichloromethane With N,N,N',N'',N'''-pentamethyldiethylenetriamine; water; copper hydroxide; sodium iodide In acetonitrile at 80℃; for 24h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 100℃; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 87% |
bromodichloromethane
lithium hexamethyldisilazane
(bromodichloromethyl)trimethylsilane
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at -78 - 20℃; Inert atmosphere; | 86% |
bromodichloromethane
3-phenyl-1-(phenylmethyl)-1H-indole
Conditions | Yield |
---|---|
Stage #1: bromodichloromethane; 3-phenyl-1-(phenylmethyl)-1H-indole With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane at 30℃; | 86% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 86% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 80℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 86% |
Conditions | Yield |
---|---|
Stage #1: 1,5-dimethyl-3-phenyl-1H-indole; bromodichloromethane With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane at 30℃; | 85% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; silver carbonate In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 84% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 84% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 80℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 84% |
1,1-diphenyl-1-propene
bromodichloromethane
2-methyl-3,3-diphenylpropenal
Conditions | Yield |
---|---|
Stage #1: 1,1-diphenyl-1-propene; bromodichloromethane With N,N,N',N'',N'''-pentamethyldiethylenetriamine; water; copper hydroxide; sodium iodide In acetonitrile at 80℃; for 24h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 100℃; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 83% |
Conditions | Yield |
---|---|
Stage #1: bromodichloromethane; C16H15N With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane at 30℃; | 82% |
Conditions | Yield |
---|---|
With tris[2-(dimethylamino)ethyl]amine; trimethylsilylazide; copper hydroxide; potassium carbonate In methanol at 50℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 82% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In acetone at 20℃; for 24h; Alkaline conditions; Inert atmosphere; | 82% |
bromodichloromethane
sodium phenylselenide
1,1-dichloro-1-phenylseleno methane
Conditions | Yield |
---|---|
In ethanol | 81% |
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