321-14-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-2-hydroxybenzoic acid is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
In the dye industry, 5-Chloro-2-hydroxybenzoic acid is utilized as an intermediate for the production of various dyes. Its chemical properties make it suitable for creating a range of colors and hues in the dye manufacturing process.
Used in Pesticide Industry:
5-Chloro-2-hydroxybenzoic acid serves as an intermediate in the development of pesticides. Its chemical structure contributes to the effectiveness of these products in controlling and managing pests, thereby protecting crops and enhancing agricultural productivity.
Used in Insecticide Applications:
As an insecticide, 5-Chloro-2-hydroxybenzoic acid is employed to control and eliminate insects that can cause damage to crops or transmit diseases. Its chemical properties make it an effective agent in protecting plants and ensuring a healthy ecosystem.
Used in Moth-Proofing Applications:
In the textile industry, 5-Chloro-2-hydroxybenzoic acid is used for moth-proofing applications. Its chemical properties help protect fabrics and garments from damage caused by moths, extending their lifespan and maintaining their quality.

Hazard

Toxic by ingestion.

InChI:InChI=1/C7H5ClO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,(H,10,11)/p-1

Synthetic route

carbon dioxide (124-38-9) + 4-chloro-phenol (106-48-9) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
Stage #1: 4-chloro-phenol With sodium hydroxide In water for 2h; Autoclave; Reflux; Stage #2: carbon dioxide In N,N-dimethyl-formamide at 80 - 145℃; under 2250.23 - 3750.38 Torr; for 15h; Autoclave; Stage #3: With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene pH=6.5;	97.65%
Stage #1: 4-chloro-phenol With Mesitol; sodium hydride In mineral oil at 100℃; for 0.0833333h; Glovebox; Stage #2: carbon dioxide In mineral oil at 185℃; under 760.051 Torr; for 2h;	85%
With potassium carbonate at 140℃; under 29420.3 Torr;

3-chlorobenzoate (535-80-8) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; under 3800.26 Torr; for 15h;	95%
With oxygen; potassium acetate; p-benzoquinone; palladium diacetate In ISOPROPYLAMIDE at 115℃; under 3800.26 Torr; for 15h; Product distribution / selectivity;	95%
Multi-step reaction with 2 steps 1: fuming nitric acid / Reduzieren des Nitrierungsprodukts mit Zinn und Salzsaeure 2: water; nitrous acid View Scheme

salicylic acid (69-72-7) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
Stage #1: salicylic acid With sulfuric acid In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-chloro-succinimide In acetonitrile at 20℃; for 2.5h; regioselective reaction;	92%
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 2h;	85%
With hydrogenchloride; sodium percarbonate; dihydrogen peroxide In dichloromethane; water at 40 - 45℃; Reagent/catalyst; Solvent; Green chemistry;	82.5%

2,5-dichlorobenzoic acid (50-79-3) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With pyridine; water; potassium carbonate; copper for 0.25h; sonication;	92%
With pyridine; copper; potassium carbonate In water for 2h; Heating;	84%
With sodium methylate at 150℃; Eintragen des Reaktionsgemisches in Wasser;
With copper(l) iodide; copper; potassium carbonate at 170℃; under 4413.05 Torr;

sodium ethyl carbonate (17201-44-4) + 4-chloro-phenol (106-48-9) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With carbon dioxide at 190℃; under 7600.51 Torr; for 6h; Time; Temperature; Pressure; Autoclave; regioselective reaction;	86.1%

2-bromo-5-chlorobenzoic acid (21739-93-5) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With copper(I) oxide; 2-pyridinealdoxime; cesium hydroxide; tetrabutylammomium bromide In water at 100℃; for 48h; Inert atmosphere;	81%

6-chloro-2-methyl-4H-chromen-4-one (69693-00-1) + furan-2,3,5(4H)-trione pyridine (1:1) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

2-methyl-4-chloroanisole (3260-85-3) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With potassium permanganate beim Erwaermen mit Jodwasserstoffsaeure;

5-chloro-2-hydroxybenzonitrile (13589-72-5) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With sulfuric acid; water at 200℃;

5,5'-thio-bis(2-hydroxy-benzoic acid) (1820-99-1) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With sulfuryl dichloride; benzene

tetrachloromethane (56-23-5) + 4-chloro-phenol (106-48-9) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With sodium hydroxide

4-chloro-phenol (106-48-9) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With tetrachloromethane; potassium hydroxide; ethanol at 140℃; im geschlossenen Rohr;
Multi-step reaction with 4 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: water; sodium hydrogencarbonate / N,N-dimethyl-formamide; diethyl ether / 0.5 h / 20 °C / Inert atmosphere 3.1: palladium diacetate; silver(I) acetate; N-tert-butoxycarbonyl-L-leucine; 2,2,2-trifluoroethanol / 1,2-dichloro-ethane / 0.08 h / 95 °C / Inert atmosphere 3.2: 18 h / 95 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere View Scheme
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; for 15h; Schlenk technique; regioselective reaction;
With tetrachloromethane; sodium hydroxide; copper

5-chloroanthranilic acid (635-21-2) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With water; cis-nitrous acid

N,N-dichloro-p-toluenesulfonamide (473-34-7) + salicylic acid (69-72-7) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With chloroform

salicylic acid (69-72-7) → 5-chloro-2-hydroxybenzoic acid (321-14-2) + 3,5-dichlorosalicylic acid (320-72-9)

Conditions	Yield
With ethanol; chlorine
With tert-butylhypochlorite In water
With ethanol beim Chlorieren; Trennung ueber die Bariumsalze;
With antimonypentachloride

salicylic acid (69-72-7) → 5-chloro-2-hydroxybenzoic acid (321-14-2) + 3-Chloro-2-hydroxybenzoic acid (1829-32-9)

Conditions	Yield
With sodium carbonate bei der Chlorierung;
With sodium hydroxide; sodium hypochlorite at 20℃; for 2.5h; pH > 12; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With N-chlorotriethylammonium chloride In trifluoroacetic acid Ambient temperature; Yield given. Yields of byproduct given;

2-hydroxy-benzoic acid ethyl ester (118-61-6) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With sulfuryl dichloride Behandeln mit Kalilauge;

2-acetoxy-5-chloro-benzoic acid (1734-62-9) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With sodium hydroxide; alpha cyclodextrin In water at 25℃; Rate constant; Ionic strength: 1.0 (NaCl); effect of pH, concentration of α-cyclodextrin;
With water at 25℃; Kinetics;

4-chlorosalicylate (45866-17-9) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
In ethanol; water at 25℃; Equilibrium constant;

6-chloro-2-methyl-4H-chromen-4-one (69693-00-1) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol at 20℃; Oxidation;
Multi-step reaction with 2 steps 1: 59 percent / AcONa / 2 h / 260 - 270 °C 2: 10 percent aq. NaOH / ethanol / 4 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 88 percent / Na / diethyl ether 2: 10 percent aq. KOH View Scheme

3-(6-chloro-4-oxo-4H-chromen-2-yl)-2-oxo-propionic acid ethyl ester (144880-76-2) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
With potassium hydroxide Hydrolysis;

6-Chloro-2-(3-phthalidenemethylene)chromone (144880-82-0) → 5-chloro-2-hydroxybenzoic acid (321-14-2) + benzene-1,2-dicarboxylic acid (88-99-3)

Conditions	Yield
With sodium hydroxide In ethanol for 4h; Hydrolysis; Heating;

6-chloro-2,3-dimethyl-chromen-4-one (99852-42-3) + diluted alkali → 5-chloro-2-hydroxybenzoic acid (321-14-2)

6-Chloro-chromen-2-one (2051-59-4) + potassium hydroxide → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
beim Schmelzen;

6-chloro-2,3-diphenyl-4H-chromen-4-one + KOH-solution → 5-chloro-2-hydroxybenzoic acid (321-14-2) + benzoic acid (65-85-0) + 4-chloro-2-phenacetyl-phenol

water (7732-18-5) + cis-nitrous acid (7782-77-6) + 5-chloroanthranilic acid (635-21-2) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

chlorine (7782-50-5) + nitrobenzene (98-95-3) + salicylic acid (69-72-7) → 5-chloro-2-hydroxybenzoic acid (321-14-2)

5-chlorosalicyclaldehyde (635-93-8) + chromic acid → 5-chloro-2-hydroxybenzoic acid (321-14-2)

tetrachloromethane (56-23-5) + 4-chloro-phenol (106-48-9) + furan-2,3,5(4H)-trione pyridine (1:1) + copper → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
bei Siedetemperatur;

tetrachloromethane (56-23-5) + ethanol (64-17-5) + 4-chloro-phenol (106-48-9) + KOH → 5-chloro-2-hydroxybenzoic acid (321-14-2)

Conditions	Yield
at 140℃;

5-chloro-2-hydroxybenzoic acid (321-14-2) + 3-Chloro-2-methylpropene (563-47-3) → 2-methylallyl 5-chloro-2-(2-methylallyloxy)benzoate

Conditions	Yield
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-Chloro-2-methylpropene In N,N-dimethyl-formamide at 65℃; for 21h;	100%
With potassium carbonate In N-methyl-acetamide

5-chloro-2-hydroxybenzoic acid (321-14-2) + 2-Methylphenylboronic acid (16419-60-6) → 4-hydroxy-2'-methylbiphenyl-3-carboxylic acid (25205-15-6)

Conditions	Yield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 20℃; for 12h; Suzuki-Miyaura coupling;	99%

5-chloro-2-hydroxybenzoic acid (321-14-2) → 4-chloro-2-hydroxymethylphenol (5330-38-1)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 0.75h; Heating;	97%
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 4.5h;	96%
With borane-THF; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 18h;	85%

5-chloro-2-hydroxybenzoic acid (321-14-2) + acetic anhydride (108-24-7) → 2-acetoxy-5-chloro-benzoic acid (1734-62-9)

Conditions	Yield
With sulfuric acid for 3h; Heating / reflux;	97%
With sulfuric acid	93%
With sulfuric acid	93%

5-chloro-2-hydroxybenzoic acid (321-14-2) + tributyltin chloride (1461-22-9) → C19H31ClO3Sn

Conditions	Yield
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: tributyltin chloride In methanol for 5h;	97%

zirconocene dichloride (1291-32-3) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → [Cp2Zr(μ2-O',O''C-C6H3(OH)Cl)2] (1192558-54-5)

Conditions	Yield
In hydrogenchloride; dichloromethane mixt. of zirconocene dichloride in 1 M aq. HCl and dichlorobenzoic acidin CH2Cl2 was stirred for 30 min at room temp.; organic layer was separated, dried over MgSO4, filtered, concd. in vac.,crystd. form CH2Cl2/Et2O/hexane, elem. anal.;	96.3%

5-chloro-2-hydroxybenzoic acid (321-14-2) → 5-chloro-2-hydroxy-3-nitrobenzoic acid (7195-78-0)

Conditions	Yield
With sulfuric acid; nitric acid at 20℃;	96%
With sulfuric acid; nitric acid at 0 - 20℃; for 5.66667h;	95%
With sulfuric acid; nitric acid for 6h; Ambient temperature;	90.5%

5-chloro-2-hydroxybenzoic acid (321-14-2) → 3-bromo-5-chloro-2-hydroxy benzoic acid (4068-58-0)

Conditions	Yield
With bromine In chloroform	96%
With N-Bromosuccinimide In carbon disulfide at 25℃; for 14h;
With bromine; acetic acid at 80℃; for 8h;	204.6 g
With bromine; acetic acid at 80℃; for 8h;	204.6 g

dichloromethane (75-09-2) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → 6-chloro-4H-benzo[d][1,3]dioxin-4-one (342411-03-4)

Conditions	Yield
With potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 6h; Green chemistry;	96%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 5,5-dibenzyl-2,3,4,5-tetrahydropyridine (1416767-53-7) → 6,6-dibenzyl-2-chloro-6,7,8,9-tetrahydro-5aH,11H-pyrido[2,1-b][1,3]benzoxazin-11-one

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h;	96%

5-chloro-2-hydroxybenzoic acid (321-14-2) + acetyl chloride (75-36-5) → 2-acetoxy-5-chloro-benzoic acid (1734-62-9)

Conditions	Yield
With pyridine; sulfuric acid In toluene	95.6%
With triethylamine In tetrahydrofuran at 20℃;	46.7%

sebacoyl chloride (111-19-3) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → 1,10-bis-4-chlorosalicyl-sebacate

Conditions	Yield
Stage #1: sebacoyl chloride; 5-chloro-2-hydroxybenzoic acid With pyridine In tetrahydrofuran for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2;	95%

5-chloro-2-hydroxybenzoic acid (321-14-2) + dibutyltin chloride (683-18-1) → 2C7H4ClO3(1-)*Sn(4+)*2C4H9(1-)

Conditions	Yield
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: dibutyltin chloride In methanol for 5h;	95%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 2,4-difluorophenylboronic acid (144025-03-6) → 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid (22494-42-4)

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); tetrabutylammomium bromide; potassium carbonate In ethanol; water for 8h; Concentration; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Reflux;	95%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 2-[(N,N-dimethylamino)methyl]ferrocenylmethylamine → C21H23ClFeN2O2

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide at 80℃; for 2h; Microwave irradiation;	95%

5-chloro-2-hydroxybenzoic acid (321-14-2) → methyl 5-chloro-2-hydroxybenzoate (4068-78-4)

Conditions	Yield
With sulfuric acid In methanol	94.8%
With thionyl chloride In methanol; ethyl acetate	74%
With thionyl chloride In methanol; ethyl acetate	74%

conc. H2 SO4 + 5-chloro-2-hydroxybenzoic acid (321-14-2) → methyl 5-chloro-2-hydroxybenzoate (4068-78-4)

Conditions	Yield
In methanol	94.8%

methanol (67-56-1) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → methyl 5-chloro-2-hydroxybenzoate (4068-78-4)

Conditions	Yield
With thionyl chloride for 168h; Inert atmosphere; Reflux;	94%
With sulfuric acid for 120h; Inert atmosphere; Reflux;	91%
With sulfuric acid for 120h; Reflux;	91%

5-chloro-2-hydroxybenzoic acid (321-14-2) + triphenyltin chloride (639-58-7) → C25H19ClO3Sn

Conditions	Yield
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: triphenyltin chloride In methanol for 5h;	94%

2-fluoroethyl bromide (762-49-2) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → 2-fluoroethyl 5-chloro-2-(2-fluoroethoxy)benzoate (334652-76-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 48h;	93.4%
With sodium hydride

bis(3-bromopropyl) ether (58929-72-9) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → 5-chloro-2-(2-methoxyethoxy)benzoic acid 2-methoxyethyl ester (521065-04-3)

Conditions	Yield
With potassium carbonate In ethyl acetate; acetonitrile	93%

5-chloro-2-hydroxybenzoic acid (321-14-2) + copper dichloride → 5-chloro-2-hydroxy benzoic acid copper (II) salt

Conditions	Yield
Stage #1: 5-chloro-2-hydroxybenzoic acid With sodium hydroxide In water Stage #2: copper dichloride In water for 24h;	93%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 4-cyanophenylboronic acid (126747-14-6) → 4'-cyano-4-hydroxybiphenyl-3-carboxylic acid

Conditions	Yield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 80℃; for 12h; Suzuki-Miyaura coupling;	92%

5-chloro-2-hydroxybenzoic acid (321-14-2) + dibutyltin chloride (683-18-1) → C15H22Cl2O3Sn

Conditions	Yield
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: dibutyltin chloride In methanol for 5h;	92%

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → Ti(η5-C5H5)2(C6H3Cl(O)(CO2)) (233600-03-8)

Conditions	Yield
With NaOH; catalyst: C2H5OH In ethanol; chloroform; water-d2 Kinetics; NaOH and C2H5OH added to mixt. of (C5H5)2TiCl2 and acid dissolved in CHCl3, stirred for 30 min at room temp.; dried (anhydrous MgSO4), filtered, filtrate concd. in vac., ppt. recrystd. from CH2Cl2/hexane; elem. anal.;	91.1%

5-chloro-2-hydroxybenzoic acid (321-14-2) + trimethyltin(IV)chloride (1066-45-1) → C10H13ClO3Sn

Conditions	Yield
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: trimethyltin(IV)chloride In methanol for 5h;	91%

Upstream product

• 69693-00-1 6-chloro-2-methyl-4H-chromen-4-one 
• 3260-85-3 2-methyl-4-chloroanisole 
• 13589-72-5 5-chloro-2-hydroxybenzonitrile 
• 1820-99-1 5,5'-thio-bis(2-hydroxy-benzoic acid) 
• 56-23-5 tetrachloromethane 
• 106-48-9 4-chloro-phenol 
• 635-21-2 5-chloroanthranilic acid 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 69-72-7 salicylic acid 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 50-79-3 2,5-dichlorobenzoic acid 
• 1734-62-9 2-acetoxy-5-chloro-benzoic acid 
• 45866-17-9 4-chlorosalicylate 
• 144880-76-2 3-(6-chloro-4-oxo-4H-chromen-2-yl)-2-oxo-propionic acid ethyl ester 

Downstream Products

• 4068-78-4 methyl 5-chloro-2-hydroxybenzoate 
• 63917-57-7 6-chloro-2-methyl-benzo[1,3]dioxin-4-one 
• 718612-48-7 5-chloro-2-hydroxy-benzoic acid-(4-nitro-phenyl ester) 
• 6626-92-2 5-chloro-N-(2-chlorophenyl)-2-hydroxybenzamide 
• 3438-16-2 5-chloro-2-methoxybenzoic acid 
• 33924-48-0 methyl 5-chloro-2-methoxybenzoate 
• 100334-95-0 7-chloro-1,3-dihydroxy-9H-xanthen-9-one 
• 73662-23-4 4',5-dichloro-2'-methylsalicylanilide 
• 32576-63-9 <5-D₁>-salicylic acid 
• 159794-26-0 5-chloro-N-[3-(diethylamino)propyl]salicylamide 
• 1026681-56-0 (S)-2-{(S)-2-[(S)-2-(5-Chloro-2-hydroxy-benzoylamino)-3-methyl-butyrylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester 
• 15459-50-4 4-chloro-2,6-diiodo-phenol 
• 635-93-8 5-chlorosalicyclaldehyde 
• 224814-77-1 5-chloro-N-(4-(trifluoromethyl)phenyl)-2-hydroxybenzamide 

Relevant academic research and scientific papers

Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids

A simple Pd(OAc)2 catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant has been explored. This protocol features relatively broad substrate scope and operational simplicity. The compatibility of ortho-substituted substrates is an effective complement to the previous ortho-hydroxylation reaction.

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.

A O-substituted benzoic acid meta chlorination method (by machine translation)

The present invention provides O-substituted benzoic acid meta chloride method, the O substituted benzoic acid, chlorinated reagent in the catalyst under catalysis of the chlorination reaction, to obtain the meta chlorinated product; the chlorination reaction of reaction solvent comprises organic solvent; wherein said organic solvent is acetonitrile, DMF, dichloromethane and dichloroethane in at least one of; the chlorination reagent is hydrogen peroxide - hydrochloric acid system, or hypochlorous acid and salts thereof; and the catalyst is an alkali metal carbonate, nitrate or percarbonate. The present inventors study found that, in the stated under a reaction system, can be unexpectedly high selectivity to get the 5 - position single-substituted product, and the yield of the product is high; in addition, the method of the invention does not need such as the existing technology commonly adopted through chlorine substitution method, easy to control reaction condition, and will not be a burden to personnel and the environment. The method of the invention high conversion rate of raw materials, 5 - position single-substituted good selectivity, few by-products, the production environment friendly, low cost, and is suitable for industrial mass production. (by machine translation)

Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl

Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.

Synthetic method of 5-chlorosalicylic acid

The invention discloses a synthetic method of 5-chlorosalicylic acid. The synthetic method comprises the following steps of: (1) in a mixed solvent of a water-insoluble solvent and water, adding parachlorophenol and strong base with the molar ratio of 1:1, adopting an oil-water separation method to remove water to obtain suspension liquid of parachlorophenol sodium salt; (2) adding a catalyst which can dissolve the parachlorophenol sodium salt and also can absorb carbon dioxide into the suspension liquid of the parachlorophenol sodium salt, then placing in a carbon-dioxide atmosphere, rising the temperature to 100-150 DEG C, reacting till carbon dioxide is not absorbed, cooling, removing carbon dioxide to obtain mixed liquid; (3) refining the mixed liquid to obtain 5-chlorosalicylic acid.The synthetic method disclosed by the invention has the advantages of simpleness, convenience in operation and low synthetic cost.

Improved synthesis method of 5-chlorosalicylic acid

The invention relates to an improved synthesis method of 5-chlorosalicylic acid. The improved synthesis method comprises the following steps of (a) sequentially adding an organic solvent and salicylic acid into a reaction container, heating to 80 to 130 DEG C, warming, and reducing the content of water in the reaction container to be less than 0.03%; (b) filling chlorine into the reaction container to react, wherein the filling amount of chlorine is at least equal to 90% of theoretical amount; then, cooling to 30 to 50 DEG C, and sucking and filtering; (c) refining a filter cake by the organic solvent, so as to obtain the 5-chlorosalicylic acid. The improved synthesis method has the advantages that the product only contains a small amount of unreacted chlorosalicylic acid and required 5-chlorosalicylic acid, so that the purity of the 5-chlorosalicylic acid is high; the solution after refining can be applied into chlorinating reaction, and the recycling purpose is realized; the wastewater is not produced in the whole production process, and the byproduct is not produced in the reaction process.

Carboxylation of o-, m-, and p-chlorophenols with sodium ethyl carbonate

The possibility for the synthesis of 5-chloro-2-hydroxybenzoic, 4-chloro-2-hydroxybenzoic, and 3-chloro-2-hydroxybenzoic acids via regioselective carboxylation of p-, m-, and o-chlorophenols, respectively, with sodium ethyl carbonate has been demonstrated

Synthesis process of glibenclamide intermediate 5-chlorosalicylic acid

The invention provides a synthesis process of a glibenclamide intermediate 5-chlorosalicylic acid. The synthesis process is characterized by comprising the following steps of adding salicylic acid and chlorobenzene into a reaction tank according to the weight ratio of 1:(5-10), and meanwhile adding acetic acid, wherein the adding weight ratio of salicylic acid to acetic acid is 1:(0.02-0.03); heating to 20 DEG C, and dissolving by stirring; heating to 70-85 DEG C, reacting for 3 hours by preserving the heat, and meanwhile introducing chlorine gas once every half an hour, wherein the weight ratio of salicylic acid to the chlorine gas is 1:(0.4-0.6); after ending reaction, cooling, and filtering by swinging to obtain wet 5-chlorosalicylic acid; and carrying out vacuum drying to obtain 5-chlorosalicylic acid with the yield of 80-90%. The synthesis process of the glibenclamide intermediate 5-chlorosalicylic acid has the advantages of simplicity in operation, high repeatability and high production yield.

A versatile approach for the synthesis of para -substituted arenes via palladium-catalyzed C-H functionalization and protodecarboxylation of benzoic acids

While a great number of ortho C-H functionalization reactions have been developed and several breakthroughs have been achieved in meta C-H activation, para C-H functionalization is still in its infancy stage. In this article, a versatile strategy for the synthesis of para-substituted arenes has been developed via a tandem process consisting of palladium-catalyzed C-H functionalization and subsequent copper-catalyzed protodecarboxylation of benzoic acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the para positions of arenes bearing a variety of substituents.