Conditions | Yield |
---|---|
With tetrapropylammonium nonabromide In dichloromethane at 23℃; for 0.5h; Inert atmosphere; | 95% |
With sodium vanadate; aluminum tri-bromide; tetrabutylammomium bromide; oxygen In 1,4-dioxane; water at 80℃; for 8h; Reagent/catalyst; Solvent; Temperature; | 93.1% |
With 1-butyl-3-methylpyridinium tribromide at 20℃; for 1h; | 89% |
Conditions | Yield |
---|---|
With sodium chlorite; sodium methylate In dimethyl sulfoxide | 84% |
5-bromo-2-iodo-benzoic acid
5-bromosalicyclic acid
Conditions | Yield |
---|---|
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 100℃; for 6h; | 77% |
2-hydroxy-5-bromobenzaldehyde oxime
A
5-bromosalicyclic acid
B
5-bromosalicyclaldehyde
Conditions | Yield |
---|---|
With calcium hypochlorite; montmorillonite K-10 In chloroform at 20℃; for 4h; | A 2.5% B 69% |
A
N-methyl-N-phenylpropanamide
B
5-bromosalicyclic acid
C
5-bromo-2-hydroxypropiophenone
Conditions | Yield |
---|---|
With water; sodium hydride In tetrahydrofuran for 24h; Reflux; | A 60% B 43% C n/a |
Conditions | Yield |
---|---|
With sodium hydroxide |
n-butyllithium
diethyl ether
2,4-dibromophenol
5-bromosalicyclic acid
Conditions | Yield |
---|---|
anschliessend Behandeln mit festem Kohlendioxid; |
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether anschliessendes Behandeln mit CO2; |
phenyl 5-bromo-2-hydroxybenzoate
5-bromosalicyclic acid
Conditions | Yield |
---|---|
bei der Verseifung; |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium nitrite |
Conditions | Yield |
---|---|
With bromine; iodine; acetic acid | |
With bromine In acetic acid | |
With N-Bromosuccinimide; 1-n-butyl-3-methylimidazolim bromide for 0.0333333h; Ionic liquid; | |
With sulfuric acid; bromine at 20℃; for 1h; Reagent/catalyst; Temperature; | A 94.5 %Chromat. B 5 %Chromat. |
Stage #1: salicylic acid In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 16h; Solvent; |
diethyl ether
propyllithium
2,4,6-tribromophenol
5-bromosalicyclic acid
Conditions | Yield |
---|---|
anschliessend Behandeln mit festem Kohlendioxid; |
Conditions | Yield |
---|---|
With chloroform; bromine Behandeln mit alkoh. Kali; |
Conditions | Yield |
---|---|
With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide In acetonitrile for 5h; Ambient temperature; Yield given. Yields of byproduct given; | |
With sulfuric acid; bromine; acetic acid at 30℃; for 2h; Temperature; | A 6.2 %Chromat. B 87.6 %Chromat. |
salicylic acid
A
3-bromosalicylic acid
B
5-bromosalicyclic acid
C
3,5-dibromosalicylic acid
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile for 5h; Ambient temperature; | |
With sulfuric acid; bromine; acetic acid at 30 - 60℃; for 0.5h; | A 5.9 %Chromat. B 88.1 %Chromat. C 5.8 %Chromat. |
With sulfuric acid; bromine at 3 - 25℃; for 1.5h; Reagent/catalyst; Temperature; | A 1 %Chromat. B 96 %Chromat. C 3 %Chromat. |
Stage #1: salicylic acid With sulfuric acid In dichloromethane at 20℃; for 0.0833333h; Stage #2: With N-Bromosuccinimide In dichloromethane at 20℃; for 0.5h; |
6-bromo-2,3-dimethyl-4H-chromen-4-one
5-bromosalicyclic acid
6-bromo-3-ethyl-2-methyl-4H-chromen-4-one
A
5-bromosalicyclic acid
B
2-Pentanone
Conditions | Yield |
---|---|
Behandeln des Produktes mit Wasser; |
sulfuric acid
bromine
acetic acid
salicylic acid
5-bromosalicyclic acid
water
hydrogen bromide
dihydrogen peroxide
salicylic acid
A
5-bromosalicyclic acid
B
3,5-dibromosalicylic acid
bromine
salicylic acid
A
5-bromosalicyclic acid
B
3,5-dibromosalicylic acid
bromine
iodine
acetic acid
salicylic acid
A
5-bromosalicyclic acid
B
3,5-dibromosalicylic acid
Conditions | Yield |
---|---|
With potassium carbonate at 140℃; under 29420.3 Torr; |
5-bromosalicyclic acid
Conditions | Yield |
---|---|
With overheated steam |
5-bromosalicyclic acid
Conditions | Yield |
---|---|
With hydrogen bromide; copper |
glucose
B
5-bromosalicyclic acid
Conditions | Yield |
---|---|
With potassium permanganate Behandeln der entstandenen Glykosido-5-brom-salicylsaeure mit Salzsaeure; |
Conditions | Yield |
---|---|
With potassium hypobromite |
methanol
5-bromosalicyclic acid
5-bromo-2-hydroxy-benzoic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid Heating; | 100% |
Stage #1: 5-bromosalicyclic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 50℃; for 2h; Stage #2: methanol for 0.5h; Solvent; Temperature; | 100% |
With sulfuric acid for 5h; Heating; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; for 17h; | 100% |
5-bromosalicyclic acid
phenylboronic acid
4-hydroxybiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate In water at 20℃; for 2h; | 99% |
With [Pd(N-(3-chloro-2-quinoxalinyl)-N'-(2,6-diisopropylphenyl)imidazolium)(PPh3)Cl2]; potassium carbonate In water at 70℃; for 3h; Catalytic behavior; Suzuki-Miyaura Coupling; | 98% |
With potassium carbonate In water at 60℃; for 3h; Suzuki-Miyaura Coupling; | 96% |
5-bromosalicyclic acid
4-methylphenylboronic acid
5-(4-tolyl)salicylic acid
Conditions | Yield |
---|---|
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling; Green chemistry; | 99% |
With potassium carbonate In water at 20℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry; | 95% |
With potassium phosphate; 2-(dicyclohexylphosphino)biphenyl based D-gluconamide; palladium diacetate In water at 80℃; for 16h; | 87% |
5-bromosalicyclic acid
2,4-difluorophenylboronic acid
2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With 2-[5-(4-methylphenyl)isoxazol-3-yl]-5-(5-phenylisoxazol-3-yl)-1,3,4-oxadiazole·2PdCl2; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.0166667h; Suzuki Coupling; | 99% |
With potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 75℃; Temperature; Solvent; Reagent/catalyst; Sonication; Cooling; | 98.37% |
With C11H8Cl4N2O3Pd; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.0833333h; Suzuki Coupling; | 97% |
5-bromosalicyclic acid
4-methoxyphenylboronic acid
4-hydroxy-4'-methoxy-[1,1'-biphenyl]-3-carboxylic acid
Conditions | Yield |
---|---|
With 2C2H5NO2*Pd(2+)*2Cl(1-); sodium hydrogencarbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling; Green chemistry; | 99% |
With [Pd(N-(3-chloro-2-quinoxalinyl)-N'-(2,6-diisopropylphenyl)imidazolium)(PPh3)Cl2]; potassium carbonate In water at 70℃; for 3h; Catalytic behavior; Suzuki-Miyaura Coupling; | 98% |
With potassium carbonate In water at 20℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry; | 96% |
Conditions | Yield |
---|---|
Stage #1: hexadecanyl bromide With lithium In diethyl ether at -10℃; for 2h; Inert atmosphere; Stage #2: With copper(l) iodide In diethyl ether at 0℃; for 1h; Inert atmosphere; Stage #3: 5-bromosalicyclic acid In diethyl ether at 60℃; for 4h; Inert atmosphere; | 98.1% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane | 98% |
5-bromosalicyclic acid
alpha-bromo-3,4-difluorotoluene
3,4-difluorobenzyl 5-bromo-2-(3,4-difluorobenzyloxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 55℃; for 16h; Inert atmosphere; | 98% |
With potassium carbonate In acetone at 20℃; for 15.5h; Product distribution / selectivity; Reflux; |
Conditions | Yield |
---|---|
Stage #1: 1-Bromodocosane With lithium In diethyl ether at -10℃; for 2h; Inert atmosphere; Stage #2: With copper(l) iodide In diethyl ether at 10℃; for 1h; Inert atmosphere; Stage #3: 5-bromosalicyclic acid In diethyl ether at 60℃; for 12h; Inert atmosphere; | 97.9% |
Conditions | Yield |
---|---|
With [Pd(N-(3-chloro-2-quinoxalinyl)-N'-(2,6-diisopropylphenyl)imidazolium)(PPh3)Cl2]; potassium carbonate In water at 70℃; for 3h; Catalytic behavior; Suzuki-Miyaura Coupling; | 97% |
5-bromosalicyclic acid
4-fluoroboronic acid
2-hydroxy-5-(4'-fluorophenyl)benzoic acid
Conditions | Yield |
---|---|
With sodium carbonate; palladium dichloride In water at 20℃; for 3h; | 96% |
With potassium carbonate In water at 20℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry; | 95% |
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling; Green chemistry; | 91% |
o-fluorobenzyl bromide
5-bromosalicyclic acid
2-fluorobenzyl 5-bromo-2-(2-fluorobenzyloxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 55℃; for 16h; Inert atmosphere; | 96% |
With potassium carbonate In acetone at 70℃; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h; Inert atmosphere; Schlenk technique; Glovebox; | 75% |
With potassium carbonate In N,N-dimethyl-formamide at 22℃; for 18h; |
5-bromosalicyclic acid
benzyl bromide
phenylmethyl 5-bromo-2-[(phenylmethyl)oxy]benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 95% |
With potassium carbonate In acetone at 55℃; for 16h; Inert atmosphere; | 88% |
With potassium carbonate In acetone at 70℃; Product distribution / selectivity; | |
With caesium carbonate In acetone for 2h; Reflux; | 15 g |
Conditions | Yield |
---|---|
With dihydrogen peroxide In diethyl ether; water at 20℃; | 93.3% |
formaldehyd
5-bromosalicyclic acid
5,5'-dibromo-3,3'-dicarboxy-2,2'-dihydroxydiphenylmethane
Conditions | Yield |
---|---|
In methanol 1.) 0 deg C, 2 h, 2.) RT, 14 h; | 93% |
With sulfuric acid 1.) methanol, 1 h, 2.) methanol, water, 0 deg C, 4 h; Yield given. Multistep reaction; |
5-bromosalicyclic acid
3,5-difluorophenylboronic acid
Conditions | Yield |
---|---|
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling; Green chemistry; | 93% |
With potassium carbonate In water at 20℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry; | 91% |
5-bromosalicyclic acid
5-bromo-2-chlorobenzoic acid
Conditions | Yield |
---|---|
With tetrachloromethane; molybdenum hexacarbonyl In dimethyl sulfoxide at 150℃; for 6h; Reagent/catalyst; Solvent; Autoclave; | 92.1% |
Conditions | Yield |
---|---|
With sulfuric acid In water at 20℃; for 0.666667h; | 92% |
With sulfuric acid | 88% |
With sulfuric acid | 88% |
Conditions | Yield |
---|---|
With potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 6h; Green chemistry; | 92% |
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran Suzuki coupling; Inert atmosphere; Reflux; chemoselective reaction; | 91% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux; | 91% |
5-bromosalicyclic acid
4-cyanobenzyl bromide
4-cyanobenzyl 5-bromo-2-(4-cyanobenzyloxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 55℃; for 16h; Inert atmosphere; | 91% |
With potassium carbonate In acetone at 55℃; for 18h; |
Conditions | Yield |
---|---|
With sodium carbonate; palladium at 80℃; for 5h; | 90% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 78℃; for 6h; | 90% |
Conditions | Yield |
---|---|
In acetonitrile at 30℃; Inert atmosphere; Sealed tube; Electrochemical reaction; Sonication; | 90% |
Conditions | Yield |
---|---|
In acetonitrile at 30℃; Inert atmosphere; Sealed tube; Electrochemical reaction; Sonication; | 90% |
Conditions | Yield |
---|---|
With sodium chloride; sulfuric acid; acetic anhydride In water; ethyl acetate | 89% |
With sodium chloride; sulfuric acid; acetic anhydride In water; ethyl acetate | 88% |
Conditions | Yield |
---|---|
88.7% |
1. | ivn-mus LD50:100 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04478 . |
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