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inquiryTrimethyl borate
3,4,5-trifluoro-1-bromobenzene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 5 - 20℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -30 - -27℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h; Temperature; | 82% |
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran; ethylene dibromide at 5 - 25℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; ethylene dibromide at -30 - -27℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethylene dibromide at 20℃; for 4h; Temperature; Inert atmosphere; | 81% |
With magnesium In diethyl ether Grignard-comp. prepd. from Br-compd. and Mg in ether at 0 °C was added dropwise to 1.5 equiv. of pre-cooled (0 °C) soln. of B(OMe)3 in ether, mixt. was maintained at 0-10 °C for 1 h and allowed to warm up to 20 °C; pouring into 10 % HCl, org. layer was sepd., aq. layer was twice extd. with ether, extracts were combined, dried with MgSO4, evapd. under vac., end-product was contaminated with dehydration product; | |
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran at 25 - 35℃; for 7h; Grignard Reaction; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -5 - 25℃; for 4.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 25 - 50℃; for 1h; | |
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In 2-methyltetrahydrofuran at 20 - 80℃; for 4h; Inert atmosphere; Stage #2: Trimethyl borate In 2-methyltetrahydrofuran at -5 - 20℃; for 2.5h; Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water at 20 - 50℃; for 1h; |
Trimethyl borate
3,4,5-trifluorophenylmagnesium bromide
3,4,5-trifluoro-1-bromobenzene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3,4,5-trifluorophenylmagnesium bromide; 3,4,5-trifluoro-1-bromobenzene With magnesium In tetrahydrofuran at 5 - 15℃; for 3h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran at -20 - 25℃; for 15h; Temperature; Inert atmosphere; | 82% |
Trimethyl borate
water
3,4,5-trifluoro-1-bromobenzene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3,4,5-trifluoro-1-bromobenzene With iodine; magnesium In 2-methyltetrahydrofuran at 40 - 50℃; Stage #2: Trimethyl borate In 2-methyltetrahydrofuran at 10 - 20℃; for 8h; Stage #3: water With hydrogenchloride In 2-methyltetrahydrofuran Temperature; | 78% |
Triisopropyl borate
3,4,5-trifluoro-1-bromobenzene
A
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium In diethyl ether Grignard reaction; Stage #2: Triisopropyl borate In diethyl ether at -30 - 10℃; for 0.5h; boronation; Stage #3: With hydrogenchloride In diethyl ether at 20℃; for 1h; Hydrolysis; Title compound not separated from byproducts; |
3,4,5-trifluoro-1-bromobenzene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3,4,5-trifluoro-1-bromobenzene With magnesium Stage #2: With Trimethyl borate Stage #3: With hydrogenchloride In water |
tris(3,4,5-trifluorophenyl)boroxine
water
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
In acetonitrile | |
In diethyl ether |
Trimethyl borate
3,4,5-trifluorophenylmagnesium bromide
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; |
A
tris(3,4,5-trifluorophenyl)boroxine
B
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
at 20℃; for 144h; |
A
tris(3,4,5-trifluorophenyl)boroxine
B
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
at 20℃; for 144h; |
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide Suzuki-Miyaura coupling; Heating; | 100% |
With tripotassium phosphate "n" hydrate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide Suzuki-Miyaura coupling; Reflux; Inert atmosphere; | 100% |
With tripotassium phosphate "n" hydrate; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide Suzuki-Miyaura Coupling; Reflux; Inert atmosphere; | 100% |
para-bromoacetophenone
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran for 2h; Suzuki Coupling; Inert atmosphere; Reflux; | 100% |
With 4-methoxy-6-(((methyl-2-pyridinylmethyl)imino)methyl)phenol; palladium diacetate; potassium hydroxide In ethanol; water for 1h; Suzuki-Miyaura Coupling; Reflux; | 99% |
With C34H54N2O2; palladium diacetate; potassium carbonate In water; acetone for 1h; Suzuki Coupling; Reflux; Green chemistry; | 98% |
para-iodoanisole
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With sodium carbonate In ethanol; water at 80℃; for 0.25h; Catalytic behavior; Suzuki-Miyaura Coupling; | 100% |
2-bromo-9H-fluorene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With C35H40N4O9(2+)*2Cl(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Suzuki Coupling; Green chemistry; | 99% |
With potassium tert-butylate In ethanol; water Reflux; | 98% |
With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 97% |
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; | 97% |
1,2,4,5-tetrafluoro-3-iodobenzene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; XPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 99% |
1,3,5-trifluoro-2-iodobenzene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 99% |
2-Chloroaniline
3,4,5-trifluorophenylboronic acid
3’,4’,5’-trifluoro-[1,1’-biphenyl]-2-amine
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate; palladium dichloride In water; isopropyl alcohol at 25 - 85℃; for 5.25h; Reagent/catalyst; Temperature; Inert atmosphere; | 99% |
2-Chloronitrobenzene
3,4,5-trifluorophenylboronic acid
2-nitro-3',4',5'-trifluoro-1,1'-biphenyl
Conditions | Yield |
---|---|
With potassium tert-butylate; C33H46Cl2N4Pd In 2-methyltetrahydrofuran at 100℃; for 3h; Solvent; Reagent/catalyst; Temperature; | 98% |
With potassium phosphate tribasic trihydrate; (2-(anthracen-9-yl)-1H-inden-3-yl)dicyclohexylphosphine; palladium diacetate In water; isopropyl alcohol; toluene at 90℃; for 16h; Catalytic behavior; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 96% |
With diamminedichloropalladium(II); triphenylphosphine; sodium hydroxide In tetrahydrofuran; water for 10h; Reagent/catalyst; Suzuki Coupling; Reflux; Inert atmosphere; | 95% |
4-bromo-benzaldehyde
3,4,5-trifluorophenylboronic acid
4-(3,4,5-trifluorophenyl)benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 75℃; for 3h; Suzuki-Miyaura Coupling; | 98% |
With sodium hydrogencarbonate In water at 90℃; for 0.166667h; Suzuki Coupling; Green chemistry; | 93% |
With sodium hydrogencarbonate In ethanol; water at 70℃; for 4h; Catalytic behavior; Suzuki Coupling; | 93% |
2,7-dibromo-9H-fluorene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In ethanol; water at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; Sealed tube; | 98% |
With potassium tert-butylate In ethanol; water Reflux; | 96% |
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; | 96% |
2,3,5,6-tetrafluoropyridin-4-yliodine
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 98% |
9,9-bis-(n-butyl)-2,7-dibromofluorene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With C35H40N4O9(2+)*2Cl(1-); palladium diacetate; potassium hydroxide In ethanol at 100℃; for 1.5h; Suzuki Coupling; Green chemistry; | 98% |
With 1-[2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)ethyl]-3-[2-hydroxy-(2,4-dichlorophenyl)ethyl]imidazolium bromide; potassium tert-butylate; potassium carbonate; palladium dichloride In tetrahydrofuran; water at 60 - 90℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; | 98% |
With potassium tert-butylate In ethanol; water Reflux; | 97% |
2-Chlorobenzonitrile
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; tricyclohexylphosphine tetrafluoroborate; sodium hydroxide In water; toluene at 85℃; for 12h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere; | 98% |
With potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; tricyclohexylphosphine tetrafluoroborate In water; isopropyl alcohol; toluene at 100℃; for 12h; Temperature; Inert atmosphere; | 92% |
o-nitroiodobenzene
3,4,5-trifluorophenylboronic acid
2-nitro-3',4',5'-trifluoro-1,1'-biphenyl
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; palladium dichloride In methanol at 40℃; | 98% |
(R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; catacxium A In 1,2-dimethoxyethane; water at 100℃; for 18h; Inert atmosphere; Sealed tube; | 98% |
iodobenzene
3,4,5-trifluorophenylboronic acid
3,4,5-trifluoro-1-1’-biphenyl
Conditions | Yield |
---|---|
With sodium t-butanolate In water at 28℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling; Irradiation; | 97% |
3,4,5-trifluorophenylboronic acid
3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl
Conditions | Yield |
---|---|
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); water; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; Sealed tube; | 97% |
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); sodium carbonate In 1,4-dioxane; water at 110℃; for 0.583333h; Inert atmosphere; Microwave irradiation; | 97% |
para-bromotoluene
3,4,5-trifluorophenylboronic acid
3',4',5'-trifluoro-4-methyl-1,1'-biphenyl
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 80℃; for 0.75h; Suzuki Coupling; | 96% |
With Ph2P(CH2CH2O)22CH3; triethylamine; palladium dichloride In water at 80℃; for 4h; Suzuki coupling; Inert atmosphere; | 68% |
ethyl benzo[h]quinoline-10-carboxylate
3,4,5-trifluorophenylboronic acid
10-(3,4,5-trifluorophenyl)benzo[h]quinoline
Conditions | Yield |
---|---|
With tris(triphenylphosphine)rhodium(I) chloride; copper(l) chloride In toluene at 130℃; for 30h; Inert atmosphere; | 96% |
2,2',7,7'-tetrabromo-9,9'-spirobifluorene
3,4,5-trifluorophenylboronic acid
2,2',7,7'-tetrakis(3,4,5-trifluorophenyl)spiro-9,9'-bifuorene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux; | 96% |
10,10'-dibromo-9,9'-bianthryl
3,4,5-trifluorophenylboronic acid
10,10'-bis(3,4,5-trifluorophenyl)-9,9'-bianthracene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In tetrahydrofuran for 24h; Suzuki Coupling; Inert atmosphere; Reflux; | 96% |
Conditions | Yield |
---|---|
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 100℃; for 1h; Suzuki-Miyaura Coupling; | 96% |
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With dichloro(cycloocta-1,5-diene)palladium (II); 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); potassium carbonate In methanol Suzuki cross-coupling reaction; Microwave irradiation; Inert atmosphere; | 95% |
1-bromo-4-methoxy-benzene
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 5h; Suzuki-Miyaura Coupling; Schlenk technique; | 95% |
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium hydrogencarbonate In water; N,N-dimethyl-formamide at 110℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; | 95% |
9-(5'-bromo-[2,2'-bipyridine]-5-yl)-9H-carbazole
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 85℃; for 24h; Inert atmosphere; Reflux; | 95% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 16h; Inert atmosphere; Reflux; | 95% |
3,4,5-trifluorophenylboronic acid
1-bromo-2,3,4-trifluorobenzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; CyJohnPhos In tetrahydrofuran; water; toluene at 95℃; for 60h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 95% |
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