1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol With butyl magnesium bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 70℃; for 0.166667h; | 100% |
2-(hex-1-yn-1-yl)phenol
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 2-(hex-1-yn-1-yl)phenol With N,N,N,N,-tetramethylethylenediamine; diethylzinc In toluene at 120℃; for 1h; Stage #2: With ammonium chloride In toluene | 99% |
Stage #1: 2-(hex-1-yn-1-yl)phenol With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 30h; Stage #2: With zinc(II) chloride In toluene at 120℃; for 1h; Stage #3: With ammonium chloride In water; toluene | 98% |
With caesium carbonate; copper(l) chloride In acetonitrile at 20℃; under 760.051 Torr; for 6h; | 91.8% |
Conditions | Yield |
---|---|
With copper(l) iodide; tetra-(n-butyl)ammonium iodide; potassium carbonate; palladium In toluene at 40℃; Reagent/catalyst; Temperature; Sonogashira Cross-Coupling; Inert atmosphere; | 96.6% |
With potassium carbonate at 60℃; for 1h; | 91% |
With copper(l) iodide; L-proline; sodium hydroxide In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere; Sealed tube; | 85% |
2-phenoxyhexanal
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With Amberlyst 15 In benzene Heating; | 94% |
With acetic acid; zinc(II) chloride for 0.166667h; Heating; | 24% |
n-butyl magnesium bromide
2-(methylsulfanyl)benzofuran
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride In tetrahydrofuran at 25℃; for 0.5h; Schlenk technique; Inert atmosphere; | 94% |
2-(2-formyl-phenoxy)-hexanoic acid
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 2-(2-formyl-phenoxy)-hexanoic acid With triethylamine; p-toluenesulfonyl chloride In toluene at 70 - 80℃; for 2h; Stage #2: With sodium hydroxide In water; toluene at 70 - 75℃; for 2h; | 90% |
With sodium acetate; acetic anhydride at 90 - 100℃; Temperature; Reagent/catalyst; Large scale; | 73.1% |
With sodium acetate; acetic anhydride In acetic acid for 8h; Heating; | 64% |
With sodium acetate; acetic anhydride; acetic acid Heating; |
1-hexynyl-2-(methoxymethoxy)benzene
1,3-Dimethoxybenzene
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With gold(III) chloride; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 18h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With cyclopentene In toluene at 100℃; for 10h; Inert atmosphere; regioselective reaction; | 85% |
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 105℃; for 22h; | 82% |
Conditions | Yield |
---|---|
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 82% |
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 30% |
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 70℃; for 20h; | 81% |
(2-Pentanoyloxy-benzyl)-triphenyl-phosphonium; bromide
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With sodium tert-pentoxide In toluene Heating; | 80% |
2-(hex-1-yn-1-yl)phenol
A
2-n-butylbenzo[b]furan
B
(E)-2-(1-(2-n-butyl-benzofuran-3-yl)hex-1-enyl)phenol
C
(E)-2-(2-n-butyl-2-(2-n-butylbenzofuran-3-yl)vinyl)phenol
Conditions | Yield |
---|---|
With [Rh(OH)(cod)]2; water; tris(2,6-dimethoxyphenyl)phosphine; lithium chloride In 1,4-dioxane at 90℃; for 24h; | A 7% B 12% C 80% |
1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol
A
2-n-butylbenzo[b]furan
B
3-butylbenzo[b]-furan
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol With n-butyllithium In tetrahydrofuran at 55℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 70℃; for 0.166667h; | A 22% B 78% |
Stage #1: 1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol With n-butyllithium In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 70℃; for 0.166667h; | A 52% B 48% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 85 - 90℃; for 8h; Reagent/catalyst; Solvent; Large scale; | 77.7% |
Stage #1: methyl 2-bromohexanoate; salicylaldehyde With Aliquat 336; caesium carbonate In ethyl acetate at 80℃; for 8h; Large scale; Stage #2: With sodium methylate In toluene for 5h; Reflux; Large scale; | 38.6% |
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With tert-butylisonitrile; palladium diacetate; caesium carbonate In acetonitrile at 20℃; for 15h; | 76% |
Conditions | Yield |
---|---|
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine; cobalt(II) bromide; zinc dibromide; 1,2-bis-(dicyclohexylphosphino)ethane In acetonitrile at 20℃; under 760.051 Torr; for 24h; Schlenk technique; Irradiation; | 75% |
2-(2-chloroacetyl)phenol
butyl magnesium bromide
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 2-(2-chloroacetyl)phenol; butyl magnesium bromide In tetrahydrofuran; toluene at 20 - 55℃; for 1.5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; toluene | 66% |
methyl 2-(2-formylphenoxy)hexanoate
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 5h; Reagent/catalyst; Solvent; Reflux; | 65.1% |
Multi-step reaction with 2 steps 1: K2CO3 / H2O; methanol / 2 h / Heating 2: Ac2O, AcONa, AcOH / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 84 percent / aq. KOH / 2 h / Heating 2: 64 percent / Ac2O, AcONa / acetic acid / 8 h / Heating View Scheme |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere; | 65% |
1,2,3-trimethoxybenzene
1-hexynyl-2-(methoxymethoxy)benzene
A
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With gold(III) chloride; silver(I) triflimide In dichloromethane at 20℃; for 18h; Inert atmosphere; | A 11% B 64% |
Conditions | Yield |
---|---|
In methanol for 1h; Ambient temperature; | 62% |
sodium phenoxide
A
2-n-butylbenzo[b]furan
B
(4-iodophenyl)(phenyl)iodonium trifluoromethanesulfonate
Conditions | Yield |
---|---|
In methanol at 0 - 20℃; for 12h; Cyclization; | A 62% B n/a |
n-butyllithium
2-chlorobenzo[b]furan
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0) In hexane at 40℃; for 24h; Inert atmosphere; Sealed tube; | 59% |
1,2,3-trimethoxybenzene
1-hexynyl-2-(methoxymethoxy)benzene
A
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With platinum(II) chloride; cyclo-octa-1,5-diene In dichloromethane at 30℃; for 22h; Reagent/catalyst; Inert atmosphere; | A 11% B 58% |
cyclohexenone
2-(hex-1-yn-1-yl)phenol
B
2-n-butylbenzo[b]furan
C
(E)-2-(1-(2-n-butyl-benzofuran-3-yl)hex-1-enyl)phenol
D
(E)-2-(2-n-butyl-2-(2-n-butylbenzofuran-3-yl)vinyl)phenol
Conditions | Yield |
---|---|
With tol-BINAP; [Rh(OH)(cod)]2; water; lithium chloride In 1,4-dioxane at 90℃; for 6h; | A 9% B 14% C 2% D 47% |
Conditions | Yield |
---|---|
In water; acetone; acetonitrile for 24h; Sonogashira reaction; Inert atmosphere; Photolysis; | A 42% B 16 %Chromat. |
In water; acetone for 24h; Inert atmosphere; Photolysis; | A 30 %Chromat. B 45 %Chromat. |
1,2,3-trimethoxybenzene
1-hexynyl-2-(methoxymethoxy)benzene
A
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With (triphenylphosphine)gold(I) chloride; silver(I) triflimide In dichloromethane at 20℃; for 18h; Inert atmosphere; | A 37% B 27% C 18% |
Conditions | Yield |
---|---|
With cis-[((2,4,6-trimethylphenylamino)(morpholino)methylidene)]PdCl2(2,4,6-trimethylphenylisonitrile); mercury; sodium hydroxide In 1,4-dioxane; water at 80℃; for 4h; Reagent/catalyst; Hiyama Coupling; | 24% |
Conditions | Yield |
---|---|
With n-butyllithium 1) Et2O, 0 deg C, 1 h; Yield given. Multistep reaction; |
2-n-butylbenzo[b]furan
4-methoxy-benzoyl chloride
2-n-butyl 3-(4-methoxy benzoyl)-benzofuran
Conditions | Yield |
---|---|
With iron(III) chloride In water; toluene | 100% |
With iron(III) chloride In water; toluene |
2-n-butylbenzo[b]furan
(R)-2-butyl-2,3-dihydrobenzofuran
Conditions | Yield |
---|---|
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (x)BF4*C27H27N2(1+); potassium tert-butylate; hydrogen In hexane; toluene at 25℃; under 7500.75 Torr; for 16h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction; | 100% |
With hydrogen; C39H36IrNOP(1+)*C32H12BF24(1-) In dichloromethane at 25℃; under 38002.6 Torr; for 24h; Autoclave; Glovebox; enantioselective reaction; | 93% |
2-n-butylbenzo[b]furan
4-methoxy-benzoyl chloride
2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -20 - -15℃; for 10h; Reflux; | 92.8% |
With aluminum (III) chloride In 1,2-dichloro-ethane at -10 - 60℃; for 7h; Temperature; | 92% |
With aluminum (III) chloride In 1,2-dichloro-ethane at -20 - -10℃; for 10h; Reflux; Large scale; | 40.1% |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 2: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme |
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 3,5-diiodo-4-(2-chloroethoxy)benzoyl chloride With aluminum (III) chloride In dichloromethane at -5℃; for 1h; Stage #2: 2-n-butylbenzo[b]furan In dichloromethane at -5℃; for 13h; | 85.4% |
2-n-butylbenzo[b]furan
4-methoxy-benzoyl chloride
2-n-butyl 3-(4-methoxy benzoyl)-benzofuran
Conditions | Yield |
---|---|
With aluminum (III) chloride In 1,2-dichloro-ethane at -20 - -10℃; Solvent; Temperature; Reagent/catalyst; Large scale; | 81.2% |
With aluminum (III) chloride In dichloromethane at 20℃; for 24h; Inert atmosphere; | 71% |
Stage #1: 2-n-butylbenzo[b]furan With carbon disulfide for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: 4-methoxy-benzoyl chloride With tin(IV) chloride at 0 - 20℃; for 75h; | 64% |
Stage #1: 4-methoxy-benzoyl chloride With aluminum (III) chloride In dichloromethane at 0 - 5℃; for 1h; Stage #2: 2-n-butylbenzo[b]furan In dichloromethane at 5 - 25℃; for 2h; | 10.6 g |
2-n-butylbenzo[b]furan
3-bromo-2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 15h; | 81% |
With N-Bromosuccinimide In chloroform; acetonitrile at -8℃; for 1h; | 80% |
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; for 8h; | 49% |
Conditions | Yield |
---|---|
With gold(III) chloride; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 18h; Inert atmosphere; | 79% |
phosgene
2-n-butylbenzo[b]furan
1,1-dichloroethane
2-n-butyl 3-(4-methoxy benzoyl)-benzofuran
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; aluminium chloride In water; methoxybenzene | 78.7% |
2-n-butylbenzo[b]furan
4-bromo-benzaldehyde
4-(2-butylbenzofuran-3-yl)benzaldehyde
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 78% |
2-n-butylbenzo[b]furan
2-butyl-2,3-dihydrobenzofuran
Conditions | Yield |
---|---|
With ruthenium; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; under 22502.3 Torr; for 48h; Autoclave; chemoselective reaction; | 75% |
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); potassium tert-butylate; hydrogen; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In hexane at 60℃; under 48754.9 Torr; for 18h; Autoclave; | |
With hydrogen In neat (no solvent) at 80℃; under 7500.75 Torr; for 24h; Autoclave; chemoselective reaction; | |
With hydrogen In decalin at 180℃; under 37503.8 Torr; for 16h; Autoclave; |
2-n-butylbenzo[b]furan
1-Bromonaphthalene
2-butyl-3-(1-naphthyl)benzofuran
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 74% |
Nitroethane
2-n-butylbenzo[b]furan
(E)-2-butyl-3-(2-nitrovinyl)benzofuran
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver(I) acetate In 1,2-dimethoxyethane; dimethyl sulfoxide at 100℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; regioselective reaction; | 73% |
2-n-butylbenzo[b]furan
1-(3-Bromophenyl)ethanone
1-[3-(2-butylbenzofuran-3-yl)phenyl]ethanone
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 72% |
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