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3,4-dibromofuran
3-bromofurane
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromofuran With n-butyllithium In diethyl ether at -78℃; for 0.5h; Stage #2: With water In diethyl ether Further stages.; | 55% |
With water; tert.-butyl lithium; diisopropylamine 1.) Et2O, pentane, -78 deg C, 30 min, 2.) Et2O, pentane, from -78 deg C, 1 h to RT, 2 h; Yield given. Multistep reaction; |
3-bromofurane
Conditions | Yield |
---|---|
With quinoline at 50 - 140℃; dehydrobromination/retro-Diels-Alder reaction; | 34% |
(E)-2-bromo-2-butene-1,4-diol
3-bromofurane
Conditions | Yield |
---|---|
With sodium dichromate; sulfuric acid In water Heating; | 10% |
trans-5,6-dibromo-7-oxabicyclo{2.2.1}heptane-2-exo,3-cis-dicarboxylic acid anhydride
3-bromofurane
Conditions | Yield |
---|---|
With potassium hydroxide |
3-bromofurane
Conditions | Yield |
---|---|
With potassium dichromate; sulfuric acid In water; pentane Heating; |
3-bromofurane
Conditions | Yield |
---|---|
With calcium oxide |
3-bromofurane
(5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one
(4S,5R)-4,8-dimethyl-1-(3'-furyl)-5-hydroxy-6-nonen-1-one
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0666667h; Metallation; Stage #2: (5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 0.25h; Ring cleavage; alkylation; | 98% |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine at 110℃; for 24h; | 98% |
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 24h; | 98% |
Conditions | Yield |
---|---|
Inert atmosphere; | 98% |
3-bromofurane
2-<(4aR,5R,6R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-1,5,6,8-tetramethyl-5-naphthyl>ethanal
Conditions | Yield |
---|---|
With tert.-butyl lithium In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -70 deg C, 25 min; | 97% |
3-bromofurane
tert-butyl carbamate
N-(3-furyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine at 110℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With Cu[9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene]I; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; Sonogashira Cross-Coupling; Inert atmosphere; | 96% |
With pyrrolidine; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 120℃; for 7h; Heck alkynylation; Inert atmosphere; | 100 %Chromat. |
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at -78℃; for 2.1h; Rieche Formylation; | 96% |
3-bromofurane
N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide
1-(3-furyl)-2-[(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-trans-naphthyl]methylketone
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide In tetrahydrofuran; hexane at -78℃; for 1h; | 95% |
Conditions | Yield |
---|---|
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; caesium carbonate In 1,2-dimethoxyethane at 110℃; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; lithium hexamethyldisilazane In 1,2-dimethoxyethane at 110℃; Inert atmosphere; | 95% |
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating; | 75% |
3-bromofurane
4,4-dimethylcyclohexenone
3-(4,4-dimethylcyclohexa-1,5-dienyl)furan
Conditions | Yield |
---|---|
Stage #1: 4,4-dimethylcyclohexenone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere; Stage #2: 3-bromofurane In 1,4-dioxane at 110℃; Inert atmosphere; | 95% |
3-bromofurane
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalin-1-yl)-acetaldehyde In tetrahydrofuran at -78℃; for 1.5h; Further stages.; | 94% |
Conditions | Yield |
---|---|
With potassium phosphate; tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; palladium dichloride In o-xylene at 90℃; for 24h; Concentration; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 94% |
With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; potassium carbonate In dichloromethane; toluene at 100℃; for 5h; Suzuki coupling; Reflux; | 92% |
With potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 90℃; for 20h; Suzuki coupling reaction; | 91% |
Conditions | Yield |
---|---|
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether for 16h; Ambient temperature; | 93% |
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran for 3.33333h; Inert atmosphere; | 60% |
Conditions | Yield |
---|---|
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether for 16h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With n-butyllithium; deuteromethanol In tetrahydrofuran; cyclohexane at -65℃; | A 6% B 93% |
3-bromofurane
5-(2-bromo-ethyl)-1,1,4α-trimethyl-6-methylene-decahydro-naphthalene
(+)-(5S,9S,10S)-15,16-epoxy-8(17),13(16),14-labdatriene
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: 5-(2-bromo-ethyl)-1,1,4α-trimethyl-6-methylene-decahydro-naphthalene In tetrahydrofuran; hexane at -78℃; for 2h; Further stages.; | 93% |
With n-butyllithium In tetrahydrofuran at -78℃; | 93% |
Conditions | Yield |
---|---|
With potassium carbonate; triphenylphosphine; RuCl2(η6-C6H6) In 1-methyl-pyrrolidin-2-one at 120℃; for 20h; | 93% |
3-bromofurane
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
C15H23NO5
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; | 93% |
3-bromofurane
1,2-bis(2,2-diethoxyethyl) disulfide
tert.-butyl lithium
3-(2,2-diethoxy-ethylsulfanyl)furan
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane; tert.-butyl lithium In diethyl ether; pentane at -78℃; Inert atmosphere; Stage #2: 1,2-bis(2,2-diethoxyethyl) disulfide In diethyl ether; pentane at 20℃; Inert atmosphere; | 93% |
3-bromofurane
(5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one
(4R,5R)-4,8-dimethyl-1-(3'-furyl)-5-hydroxy-6-nonen-1-one
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; | 92.1% |
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0666667h; Metallation; Stage #2: (5R,6R)-6-(3-methyl-2-butenyl)-5-methyl-3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 0.25h; Ring cleavage; alkylation; | 92% |
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane With lithium diisopropyl amide In 2-methyltetrahydrofuran at -45℃; for 0.5h; Vilsmeier-Haack reaction; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In 2-methyltetrahydrofuran at -40℃; for 0.333333h; Vilsmeier-Haack reaction; Inert atmosphere; | 92% |
With trichlorophosphate 1) room temperature, 1 h; 2) 80 deg C, 2 h; | 86% |
Stage #1: 3-bromofurane With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Stage #3: With phosphoric acid In tert-butyl methyl ether; water for 0.5h; Inert atmosphere; Cooling with ice; regioselective reaction; | 84% |
3-bromofurane
1-phenylmethyl-4-piperidone
1-benzyl-4-(furan-3-yl)-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
Stage #1: 1-phenylmethyl-4-piperidone With tris-(dibenzylideneacetone)dipalladium(0); toluene-4-sulfonic acid hydrazide; lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere; Stage #2: 3-bromofurane In 1,4-dioxane at 110℃; for 5h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With tert.-butyl lithium In diethyl ether; pentane at 0 - 20℃; for 3.5h; Inert atmosphere; | 91% |
With n-butyllithium; diisopropylamine 1.) Et2O, hexane, -78 deg C, 30 min, 2.) Et2O, hexane, from -78 deg C, 1 h to RT, 2 h; Yield given. Multistep reaction; |
3-bromofurane
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 16(13->14)abeo-18a-homo-1,18-cyclo-ent-halima-5(10),14-dien-18-one In tetrahydrofuran; hexane at -78℃; Further stages.; | 91% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); 6H-dibenzo[d,f-1,3]diazepin-6-ylidene-5,7-dihydro-5,7-diphenylphosphanyl; sodium carbonate In N,N-dimethyl acetamide at 130℃; for 24h; Catalytic behavior; Heck Reaction; Schlenk technique; Inert atmosphere; | 91% |
With bis(η3-allyl-μ-chloropalladium(II)); 6H-dibenzo[d,f-1,3]diazepin-6-ylidene-5,7-dihydro-5,7-diphenylphosphanyl; sodium carbonate In N,N-dimethyl acetamide at 130℃; for 24h; Heck Reaction; Inert atmosphere; Schlenk technique; | 91% |
With NAP-Mg-Pd(0) In N,N-dimethyl-formamide at 130℃; for 8h; Reagent/catalyst; Solvent; Temperature; Heck Reaction; | 83% |
With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 140℃; for 20h; Heck reaction; | 82% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate In N,N-dimethyl acetamide; butan-1-ol at 110℃; for 20h; Suzuki Coupling; Inert atmosphere; | 91% |
3-bromofurane
4-methoxyphenyl magnesium bromide
3-(4-methoxy-phenyl)-furan
Conditions | Yield |
---|---|
With cobalt(II) chloride; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 20℃; for 1h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere; | 91% |
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran for 3.33333h; Inert atmosphere; | 77% |
3-bromofurane
methyl 2-ethylenedioxy-12-oxo-13,14,15,16-tetranor-ent-halim-5(10)-en-18-oate
methyl 15,16-epoxy-2-ethylendioxy-12SR-hydroxy-5(10),13(16),14-ent-halimatrien-18-oate
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; | 90% |
Conditions | Yield |
---|---|
Stage #1: 3-bromofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78℃; Further stages.; | 90% |
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