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inquiry(3-fluorophenyl)(mesityl)iodonium trifluoromethanesulfonate
3-fluorobromobenzene
Conditions | Yield |
---|---|
With copper(I) bromide In acetonitrile at 80℃; for 2h; | 91% |
3-fluorobromobenzene
Conditions | Yield |
---|---|
With copper(I) oxide; sulfuric acid; sodium nitrite In water; isopropyl alcohol at -10 - 0℃; for 5h; Temperature; Reagent/catalyst; Solvent; | 82.7% |
1,1,1-trifluoro-4-methyl-pent-3-en-2-one
A
2,2′-dibromo-4,4′-difluorobiphenyl
B
3-fluorobromobenzene
C
4-(2-bromo-4-fluorophenyl)-1,1,1-trifluoro-4-methylpentan-2-one
D
2-(2-bromo-4-fluorophenyl)-1,1,1-trifluoro-4-methylpent-3-en-2-ol
E
2-bromo-4-fluoro-phenol
Conditions | Yield |
---|---|
Stage #1: 2-bromo-4-fluoro-1-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at -30 - -25℃; for 0.5h; Inert atmosphere; Large scale; Stage #2: 1,1,1-trifluoro-4-methyl-pent-3-en-2-one With copper(l) iodide In tetrahydrofuran at -30 - -25℃; for 4h; Inert atmosphere; Large scale; | A 0.5% B 16% C 75% D 5% E 0.5% |
bromobenzene
A
o-fluorobromobenzene
B
3-fluorobromobenzene
C
1-Bromo-4-fluorobenzene
Conditions | Yield |
---|---|
With fluorine In trichlorofluoromethane at -78℃; for 1h; | A 23 % Chromat. B 17 % Chromat. C 60 % Chromat. |
With fluorine In trichlorofluoromethane at -78℃; for 1h; Rate constant; Product distribution; competitive reaction with benzene; | A 23 % Chromat. B 17 % Chromat. C 60 % Chromat. |
With xenon difluoride; boron trifluoride diethyl etherate In acetonitrile at -35 - 20℃; for 2.5h; Inert atmosphere; Overall yield = 56 %; |
Conditions | Yield |
---|---|
With bromobenzene; Cu-HZSM-5 zeolite at 399.9℃; Mechanism; various catalysts; | 14.3 % Chromat. |
carbon disulfide
fluorobenzene
bromine
A
o-fluorobromobenzene
B
3-fluorobromobenzene
C
1-Bromo-4-fluorobenzene
Conditions | Yield |
---|---|
at 55℃; Product distribution; |
tetrachloromethane
fluorobenzene
A
o-fluorobromobenzene
B
3-fluorobromobenzene
C
4-fluoro-1-iodobenzene
D
1-Bromo-4-fluorobenzene
Conditions | Yield |
---|---|
Product distribution; |
fluorobenzene
A
o-fluorobromobenzene
B
3-fluorobromobenzene
C
1-Bromo-4-fluorobenzene
Conditions | Yield |
---|---|
With bromine at 25℃; for 16h; Irradiation; Yield given; |
3-fluorobromobenzene
Conditions | Yield |
---|---|
With bromine at 400 - 700℃; |
bromobenzene
A
o-fluorobromobenzene
B
2-bromo-1-oxypentafluorosulfanylbenzene
C
4-bromo-1-oxypentafluorosulfanylbenzene
R
3-fluorobromobenzene
S
1,3-dibromobenzene
T
1.4-dibromobenzene
U
1-Bromo-4-fluorobenzene
V
1,2-dibromobenzene
Conditions | Yield |
---|---|
With bis(pentafluorosulfur) peroxide at 100℃; for 17h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C View Scheme |
bromobenzene
A
o-fluorobromobenzene
B
2-bromo-1,4-difluorobenzene
C
3-fluorobromobenzene
D
1-bromo-3,4-difluorobenzene
E
1-Bromo-4-fluorobenzene
Conditions | Yield |
---|---|
With xenon difluoride; boron trifluoride diethyl etherate at 0 - 25℃; Cooling with ice; | A 0.06 mmol B 0.01 mmol C 0.03 mmol D 0.004 mmol E 0.16 mmol |
benzaldehyde
A
3-fluorobromobenzene
C
benzoic acid
D
benzyl alcohol
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 40℃; for 1h; |
3-fluorobromobenzene
Conditions | Yield |
---|---|
With water; sodium hydroxide In tetrahydrofuran at 40℃; for 1h; |
Conditions | Yield |
---|---|
Stage #1: 2-Fluoroaniline With sulfuric acid; dihydrogen peroxide; bromine at 10 - 15℃; for 0.5h; Stage #2: With nitrosylsulfuric acid at 5℃; for 2h; Overall yield = 80.8 %; |
3-fluorobromobenzene
formic acid ethyl ester
bis(3-fluorophenyl)methanol
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With magnesium In tetrahydrofuran Stage #2: formic acid ethyl ester In tetrahydrofuran at 0 - 20℃; | 100% |
With magnesium In diethyl ether for 18h; Heating; | 95% |
Stage #1: 3-fluorobromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: formic acid ethyl ester In tetrahydrofuran at -78 - 0℃; for 1h; Further stages.; |
3-fluorobromobenzene
N-methyl-N-phenylformamide
2-bromo-6-fluorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With hydrogenchloride; n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - -70℃; for 2.5h; Stage #2: N-methyl-N-phenylformamide In tetrahydrofuran; hexanes at -78 - -70℃; for 2h; | 100% |
(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
3-fluorobromobenzene
(R)-tert-butyl 3-(3-fluorobenzoyl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With magnesium In tetrahydrofuran at 50 - 60℃; for 1h; Stage #2: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate In tetrahydrofuran at -78 - 20℃; for 1.5h; Stage #3: With water; ammonium chloride In tetrahydrofuran | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene; phenylboronic acid With potassium phosphate In isopropyl alcohol at 20℃; for 4h; Suzuki Coupling; Stage #2: [Pd2(μ-Cl)2{{(C2F5)2O}2H}2] In isopropyl alcohol at 20℃; for 20h; Suzuki Coupling; | 100% |
Stage #1: 3-fluorobromobenzene; phenylboronic acid With potassium phosphate In isopropyl alcohol at 20℃; for 2h; Suzuki coupling; Inert atmosphere; Stage #2: With Juliphos In isopropyl alcohol at 20℃; for 20h; Suzuki coupling; Inert atmosphere; | 100% |
With potassium phosphate tribasic trihydrate; 1-(tert-butyl)-2-(diphenylphosphaneyl)-1H-imidazole; palladium dichloride In ethanol at 60℃; for 1h; Suzuki Coupling; Inert atmosphere; Schlenk technique; | 97% |
3-fluorobromobenzene
3-[2-(trimethylsilylethynyl)]phenol
Conditions | Yield |
---|---|
Stage #1: 3-[2-(trimethylsilylethynyl)]phenol With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 3-fluorobromobenzene With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 24h; | 100% |
3-fluorobromobenzene
formic acid ethyl ester
bis(3-fluorophenyl)methanol
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; water | 99% |
Conditions | Yield |
---|---|
With N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazol-2-ylidene palladium chloride; caesium carbonate In water; isopropyl alcohol Reagent/catalyst; Suzuki-Miyaura Coupling; | 99% |
Conditions | Yield |
---|---|
With N-[2-(3,5-dimethylpyrazol-1-yl)phenyl]-N'-benzylimidazol-2-ylidene palladium chloride; potassium carbonate In water; N,N-dimethyl-formamide Reagent/catalyst; Heck Reaction; | 99% |
With potassium phosphate; C34H46Br4N8Pd2 In N,N-dimethyl-formamide at 110℃; for 4h; Heck Reaction; | 82% |
With C74H61Cl2N3Pd; triethylamine In 1,4-dioxane for 10h; Heck Reaction; | 77% |
3-fluorobromobenzene
bis(pinacol)diborane
Conditions | Yield |
---|---|
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere; | 99% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 48h; Inert atmosphere; | 31% |
With {meso-1,3-bis(1-methylethyl)-4,5-(9,10-dihydroanthraceno)imidazolin-2-ylidene}copper(I) chloride; potassium tert-butylate In tert-butyl methyl ether at 25℃; for 4h; Inert atmosphere; | 63 %Spectr. |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 0.166667h; Miyaura Borylation Reaction; Microwave irradiation; |
3-fluorobromobenzene
o-(phenylethynyl)trifluoroacetanilide
Conditions | Yield |
---|---|
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 100℃; for 0.5h; | 98% |
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 100℃; for 3h; | 98% |
quinoline-2-carbonitrile
3-fluorobromobenzene
(3-fluorophenyl)(quinolin-2-yl)methanone
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: quinoline-2-carbonitrile In tetrahydrofuran; toluene at 0 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In diethyl ether for 0.333333h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate; di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine In 1,4-dioxane; tert-Amyl alcohol Inert atmosphere; Reflux; | 98% |
With potassium phosphate; palladium diacetate; di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine In 1,4-dioxane; tert-Amyl alcohol Inert atmosphere; Reflux; | 98% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; palladium diacetate; potassium carbonate In ethanol; water at 40 - 72℃; for 4h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 80℃; for 10h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane Inert atmosphere; Stage #2: 3,6-dioxa-1,8-diaminooctane With sodium t-butanolate In 1,4-dioxane for 8h; Reflux; | 98% |
Conditions | Yield |
---|---|
With Na2{PdCl2(Ph2P(m-C6H4SO3))2}; sodium 3-(diphenylphosphanyl)benzenesulfonate; trimethyloctadecylammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In water for 20h; Heating; | 97% |
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 80℃; for 16h; Inert atmosphere; |
3-fluorobromobenzene
1-(S-phenylsulfonimidoyl)piperidine
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 20 - 100℃; Inert atmosphere; | 97% |
3-fluorobromobenzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; sodium t-butanolate In 1,4-dioxane at 110℃; for 2h; Inert atmosphere; | 96% |
acetic acid tert-butyl ester
3-fluorobromobenzene
tert-butyl α-(3-fluorophenyl)acetate
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; lithium dicyclohexylamide; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 15h; | 95% |
Conditions | Yield |
---|---|
at 20℃; for 3h; | 95% |
Conditions | Yield |
---|---|
Stage #1: 2-methylquinoline With zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Stage #2: 3-fluorobromobenzene With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; | 95% |
3-fluorobromobenzene
cyclohexylmagnesium bromide
1-cyclohexyl-3-fluorobenzene
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II) In tetrahydrofuran for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Stage #2: cyclohexylmagnesium bromide With lithium bromide In tetrahydrofuran at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 95% |
Conditions | Yield |
---|---|
With chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I); 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-1,3,2-dioxaborolane; [PdCl2(N,N’-bis-[2,6-(diisopropyl)phenyl]imidazolidin-2-ylidene){P(N,N’-bis-[2,6-(diisopropyl)phenyl]imidazol-2-ylidene)3}]; potassium 2-methylbutan-2-olate In ethanol at 80℃; for 20h; Glovebox; regioselective reaction; | 95% |
3-fluorobromobenzene
4-formylphenylboronic acid,
3'-fluoro[1,1'-biphenyl]-4-carbaldehyde
Conditions | Yield |
---|---|
With C5H6N2*Pd(2+)*2Cl(1-); potassium carbonate In ethanol; water for 0.166667h; Suzuki-Miyaura Coupling; Reflux; Schlenk technique; | 95% |
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 2-bromo-4-methylbenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Schlenk technique; | 95% |
Conditions | Yield |
---|---|
Stage #1: 3-fluorobromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: phenyl[(2-phenylsulfanyl)phenyl]methanone In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 95% |
3-fluorobromobenzene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-(3-bromo-5-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In tetrahydrofuran at 20℃; Glovebox; Inert atmosphere; Stage #2: With 2,2'-methylenebis( N,N)-dimethylpyridin-4-amine In tetrahydrofuran at 20℃; for 0.25h; Glovebox; Inert atmosphere; Stage #3: 3-fluorobromobenzene In tetrahydrofuran at 20℃; for 5h; Glovebox; Inert atmosphere; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; lithium dicyclohexylamide; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 24h; | 94% |
3-fluorobromobenzene
phenylacetylene
1-fluoro-3-(2-phenylethynyl)benzene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium acetate In dimethyl sulfoxide at 110℃; for 35h; Sonogashira Cross-Coupling; Inert atmosphere; | 94% |
With potassium phosphate; C30H37Br2N3Pd(2-) In dimethyl sulfoxide at 100℃; for 1h; Sonogashira Cross-Coupling; | 84% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 20℃; Schlenk technique; Inert atmosphere; | 83% |
With C34H40Br2N3Pd; potassium carbonate In dimethyl sulfoxide at 100℃; for 1h; Sonogashira coupling; | 59% |
With Sonogashira catalyst CMX-1 In HN(iPr)2 at 80℃; Sonogashira coupling; |
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
3-fluorobromobenzene
1,3,7-trimethyl-8-(m-fluorophenyl)-xanthine
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 140℃; for 36.1667h; Inert atmosphere; regioselective reaction; | 94% |
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