methanol
diisopropylamine borane
5-bromo-1,3-xylene
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 5-bromo-1,3-xylene In tetrahydrofuran at 70℃; Stage #3: methanol Further stages; | 89% |
Conditions | Yield |
---|---|
With Mg; H2SO4 In tetrahydrofuran; diethyl ether aryl bromide in THF was added to Mg turnings, filtered, added dropwise with stirring to trimethyl borate in ether at -70°C, the suspn. was allowed to warm to room temp. overnight, added with stirring to ice, concd. H2SO4, stirred for 30 min (Ar); shaken with ether, dried over Na2SO4, evapd., filtered, dried in vac.; elem. anal.; | 85.6% |
With Mg; iodomethane In diethyl ether under Ar atm. 1,3-dimethyl-5-bromobenzene in Et2O was added slowly to Mgturning in the presence of MeI, react. mixt. was refluxed for 6 h and a dded at -60°C to soln. B(OMe)3 in Et2O, allowed to warm slowly toroom temp. with stirring; react. mixt. was poured into 20% H2SO4, org. phase was separated, washedwith water and dried over MgSO4, solvent was removed in vacuo; | 82% |
Trimethyl borate
water
3,5-dimethyphenylmagnesium bromide
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
Stage #1: Trimethyl borate; 3,5-dimethyphenylmagnesium bromide In tetrahydrofuran at 20℃; Stage #2: water With hydrogenchloride In tetrahydrofuran; diethyl ether | 74% |
Trimethyl borate
5-bromo-1,3-xylene
water
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
Stage #1: Trimethyl borate; 5-bromo-1,3-xylene With magnesium In tetrahydrofuran at -78 - 20℃; Stage #2: water With hydrogenchloride In tetrahydrofuran; diethyl ether | 74% |
5-bromo-1,3-xylene
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With Trimethyl borate | |
Stage #1: 5-bromo-1,3-xylene With magnesium In tetrahydrofuran Stage #2: With Trimethyl borate Stage #3: With hydrogenchloride Further stages.; | |
Stage #1: 5-bromo-1,3-xylene With magnesium; methyl iodide In diethyl ether Inert atmosphere; Reflux; Stage #2: With Trimethyl borate In diethyl ether at -60 - 20℃; Inert atmosphere; | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: -78 - 20 °C 2.1: water; hydrogenchloride / tetrahydrofuran; hexane / 20 °C / pH 3 - 5 View Scheme |
2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
Stage #1: 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water for 0.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 4h; | |
Stage #1: 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 17h; |
m-xylene
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 4,4'-di-tert-butyl-2,2'-bipyridine / [Ir(COD)(OMe)]2 / tetrahydrofuran / 16 h / 80 °C 2.1: sodium periodate / tetrahydrofuran; H2O / 0.25 h 2.2: HCl / H2O; tetrahydrofuran / 4 h View Scheme | |
Multi-step reaction with 2 steps 1.1: 4,4'-di-tert-butyl-2,2'-bipyridine; pinacolborane / [(COD)Ir(OMe)]2 / cyclohexane / 24 h / 80 °C 2.1: sodium periodate / tetrahydrofuran; H2O / 0.5 h 2.2: hydrochloric acid / tetrahydrofuran; H2O / 17 h / 20 °C View Scheme |
Triisopropyl borate
5-bromo-1,3-xylene
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With N2 In tetrahydrofuran | 2.41 g (29.7%) |
With N2 In tetrahydrofuran | 2.41 g (29.7%) |
With sodium hydroxide; n-butyllithium In tetrahydrofuran; hydrogenchloride; hexane; dichloromethane | |
Stage #1: 5-bromo-1,3-xylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 25℃; for 0.333333h; Inert atmosphere; |
C26H31B3O5
A
(4-methoxy-3,5-dimethylphenyl)boronic acid
B
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With water at 25℃; Equilibrium constant; |
C25H29B3O4
A
(4-methoxy-3,5-dimethylphenyl)boronic acid
B
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With water at 25℃; Equilibrium constant; |
C38H55B3O5
A
3,5-dimethylphenyl boronic acid
B
4-methoxy-3,5-di-tert-butylphenylboronic acid pinacol ester
Conditions | Yield |
---|---|
With water at 25℃; Equilibrium constant; |
C31H41B3O4
A
3,5-dimethylphenyl boronic acid
B
4-methoxy-3,5-di-tert-butylphenylboronic acid pinacol ester
Conditions | Yield |
---|---|
With water at 25℃; Equilibrium constant; |
C25H29B3O6
A
3,5-dimethylphenyl boronic acid
B
3,4,5-trimethoxyphenylboronic Acid
Conditions | Yield |
---|---|
With water at 25℃; Equilibrium constant; |
C26H31B3O9
A
3,5-dimethylphenyl boronic acid
B
3,4,5-trimethoxyphenylboronic Acid
Conditions | Yield |
---|---|
With water at 25℃; Equilibrium constant; |
tris(3.5-dimethyl phenyl)boroxine
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With water at 25℃; Equilibrium constant; |
3,5-dimethyphenylmagnesium bromide
B
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With Triisopropyl borate In tetrahydrofuran at -55 - 20℃; Temperature; |
(3,5-dimethylphenyl)lithium
B
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With Triisopropyl borate In tetrahydrofuran at -70 - 20℃; |
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; pH=3 - 5; | |
With hydrogenchloride; water In tetrahydrofuran | 114.6 g |
3,5-dimethyphenylmagnesium bromide
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / -78 - 20 °C 2: hydrogenchloride; water / tetrahydrofuran View Scheme |
2,6-dimethylaniline
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: bromine / methanol / 20 °C 2.1: sulfuric acid / ethanol / 1 h / 7 - 20 °C 2.2: 1.5 h / 20 °C / Cooling 2.3: 20 °C / Inert atmosphere 3.1: magnesium / tetrahydrofuran / -78 - 20 °C View Scheme |
3,5-dimethylphenyl boronic acid
methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate
methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate
Conditions | Yield |
---|---|
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol; toluene at 85℃; for 15h; Suzuki-Miayura cross-coupling; | 100% |
3,5-dimethylphenyl boronic acid
(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-iodo-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methyl propan-1-one
(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methylpropan-1-one
Conditions | Yield |
---|---|
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol; toluene at 90℃; for 15h; Suzuki-Miayura cross-coupling; | 100% |
3,5-dimethylphenyl boronic acid
3,3',5,5'-tetramethyl-1,1'-biphenyl
Conditions | Yield |
---|---|
With air; palladium diacetate In methanol at 20℃; | 100% |
With potassium acetate; silver(l) oxide In methanol at 40℃; for 15h; | 99% |
With bromo-phenyl-acetic acid methyl ester; potassium fluoride; dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II) In 1,4-dioxane; water at 100℃; for 24h; | 95% |
4-(4-bromo-2-formylphenyl)piperazine-1-carboxylic acid tert-butyl ester
3,5-dimethylphenyl boronic acid
4-(3-formyl-3',5'-dimethylbiphenyl-4-yl)piperazine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane Suzuki coupling; Heating; | 100% |
7-chloro-2-cyclohexylmethylindan-1-one
3,5-dimethylphenyl boronic acid
7-(3',5'-dimethylphenyl)-2-cyclohexylmethylindan-1-one
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate In water; ethylene glycol at 125℃; for 4h; Inert atmosphere; | 100% |
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium hydroxide; tri-t-butylphosphonium tetraphenylborate complex In tetrahydrofuran; water at 65℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With Pd/C; potassium carbonate In water; N,N-dimethyl-formamide at 40℃; for 5h; Suzuki Coupling; | 99% |
With potassium carbonate In ethanol; water at 80℃; for 7h; Suzuki Coupling; | 90% |
With tris-(o-tolyl)phosphine; microencapsulated Pd(PPh3) In acetonitrile for 6h; Heating; | 83% |
With potassium phosphate tribasic trihydrate In water at 80℃; for 15h; Suzuki-Miyaura Coupling; Green chemistry; | 82% |
(Ra)-3,3’-dibromo-2,2’-dimethoxy-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In tetrahydrofuran at 75℃; for 22h; | 99% |
Stage #1: (Ra)-3,3’-dibromo-2,2’-dimethoxy-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 0.166667h; Suzuki coupling; Stage #2: 3,5-dimethylphenyl boronic acid With sodium carbonate In ethanol at 90℃; for 18h; Further stages.; | 97% |
para-bromotoluene
3,5-dimethylphenyl boronic acid
1-(4-methylphenyl)-3,5-dimethylbenzene
Conditions | Yield |
---|---|
With bis-(1-methylimidazole)palladium(II) dichloride; sodium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry; | 99% |
With sodium carbonate; 1,2-bis(2'-pyrazineethynyl)benzene palladium dichloride In water; acetonitrile at 70℃; for 6h; Suzuki coupling; | 91% |
3,5-dimethylphenyl boronic acid
3-bromoaniline
3-amino-3',5'-dimethylbiphenyl
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; cesium fluoride In tetrahydrofuran at 20℃; for 2h; Suzuki coupling; | 99% |
With cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 2h; Suzuki Coupling; | 99% |
indole-2,3-dione
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With triphenyl phosphite; [(C2H4)2Rh(acac)] In acetone for 4h; Heating; | 99% |
6-chloro-2-picoline
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 16h; Suzuki-Miyaura coupling; | 99% |
N-(5'-bromo-3'-phenylpyraz-2'-yl)pyridinium aminide
3,5-dimethylphenyl boronic acid
N-[5-(3,5-dimethylphenyl)-3-phenylpyrazin-2-yl]pyridinium aminide
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 8h; Suzuki coupling reaction; Heating; | 99% |
3'-Chloroacetophenone
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling; | 99% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate In water; acetone at 35℃; for 0.5h; Inert atmosphere; | 99% |
With bis-(1-methylimidazole)palladium(II) dichloride; sodium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry; | 99% |
With potassium carbonate In water at 80℃; for 1.5h; Suzuki Coupling; Green chemistry; | 90% |
4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole]
3,5-dimethylphenyl boronic acid
C19H13Cl2F3N4S
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; oxygen In water; dimethyl sulfoxide at 100℃; for 36h; | 99% |
Conditions | Yield |
---|---|
With C52H36F8O2Rh2 In 1,4-dioxane; water at 50℃; for 12h; optical yield given as %ee; enantioselective reaction; | 99% |
cyclohexenone
3,5-dimethylphenyl boronic acid
(R)-3-(3,5-dimethyl-phenyl)cyclohexanone
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine; potassium hydroxide In water; toluene at 20 - 40℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: 3,5-dimethylphenyl boronic acid With chlorobis(ethylene)rhodium(I) dimer; C8H16N2O4S2 In 1,4-dioxane at 50℃; for 0.25h; Inert atmosphere; Stage #2: cyclohexenone With potassium hydroxide In 1,4-dioxane; methanol at 10℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
With potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (R,Z)-1-(tert-butylsulfinyl)-2-(prop-1-enyl)benzene In methanol; water at 40℃; for 3h; Hayashi-Miyaura reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction; | 99% |
3-Bromopyridine
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With bis-(1-methylimidazole)palladium(II) dichloride; sodium hydroxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry; | 99% |
With sodium carbonate In methanol at 60℃; for 0.5h; Suzuki-Miyaura cross-coupling; | > 99 %Chromat. |
para-bromoacetophenone
3,5-dimethylphenyl boronic acid
1-(3’,5’-dimethylbiphenyl-4-yl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In water at 80℃; for 10h; Suzuki-Miyaura Coupling; Green chemistry; | 99% |
With potassium carbonate; palladium dichloride; 3,3'-dimethyl-1,1’-(1,3-phenylenedimethylene)-bis(1H-imidazolium) dichloride In water; N,N-dimethyl-formamide for 3h; Suzuki Coupling; Reflux; | 97% |
With sodium acetate In water; N,N-dimethyl-formamide for 12h; Suzuki coupling; Reflux; | 94% |
(E)-2-fluorovinyl 4-methylbenzenesulfonate
3,5-dimethylphenyl boronic acid
(E)-1-(2-fluorovinyl)-3,5-dimethylbenzene
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; tricyclohexylphosphine In 1,4-dioxane at 100℃; for 14h; Suzuki-Miyaura reaction; Inert atmosphere; stereoselective reaction; | 99% |
1-methoxy-4-(2-nitro-vinyl)-benzene
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; tert-butanesulfinylphosphine; triethylamine In ethanol at 40℃; for 10h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
9-Chloroacridine
3,5-dimethylphenyl boronic acid
9-(3,5-dimethylphenyl)acridine
Conditions | Yield |
---|---|
With potassium phosphate In toluene at 100℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 99% |
With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene Reflux; |
Conditions | Yield |
---|---|
With bis(ethylene)rhodium(I) chloride dimer; C19H23NOS; potassium hydroxide In 1,4-dioxane; water at 20 - 50℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
benzoic acid anhydride
3,5-dimethylphenyl boronic acid
3,5-dimethylbenzophenone
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; sodium hydrogencarbonate In water at 20℃; for 12h; Inert atmosphere; | 99% |
Stage #1: benzoic acid anhydride; 3,5-dimethylphenyl boronic acid With sodium hydrogencarbonate In water at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With C19H25Br2N5Pd In water at 20℃; for 36h; Inert atmosphere; | 86% |
3,5-dimethylphenyl boronic acid
1,3-diphenyl-propen-3-one
(S)-3-(3, 5-dimethylphenyl)-1,3-diphenylpropan-1-one
Conditions | Yield |
---|---|
With potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine In water; isopropyl alcohol at 40℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
3-butyl-1,2-benzisothiazole-1,1-dioxide
3,5-dimethylphenyl boronic acid
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; (S)-methyl 6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinate; oxygen In 2,2,2-trifluoroethanol at 40℃; for 12h; enantioselective reaction; | 99% |
methyl o-formylbenzoate
3,5-dimethylphenyl boronic acid
(S)-3-(3,5-dimethylphenyl)-1,3-dihydro-2-benzofuran-1-one
Conditions | Yield |
---|---|
With (R)-Me-BIPAM; tris(triphenylphosphine)ruthenium(II) chloride; potassium carbonate In water; toluene at 50℃; for 18h; Inert atmosphere; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; lithium tert-butoxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry; | 99% |
3-methylbenzyl N,N-dimethylcarbamate
3,5-dimethylphenyl boronic acid
3,3',5-Trimethyl-diphenylmethan
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; lithium tert-butoxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry; | 99% |
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