52490-15-0

Basic information

• Product Name: 2-Butyl-3-(4-hydroxybenzoyl)benzofuran
• Synonyms: (2-butyl-3-benzofuranyl)(4-hydroxyphenyl)-methanone;2-butyl-3-benzofuranyl p-hydroxyphenyl ketone;2-BUTYL-3-(P-HYDROXYLBENZONYL)-BENZOFURAN;2-BUTYL-3-(4-HYDROXYBENZOYL)-BENZOFURAN;2-BUTYL-3-(4-HYDROXYLBENZONYL)BENZOFURAN;(2-butylbenzofuran-3-yl) (4-hydroxyphenyl) ketone;2-Butyl-3-(4-hydroxybenzoyl)benzofurane;(2-Butyl-benzofuran-3-yl)-(4-hydroxy-phenyl)-methanone
• CAS NO: 52490-15-0
• Molecular Formula: C₁₉H₁₈O₃
• Molecular Weight: 294.34
• EINECS: 257-959-5
• Product Categories: BUILDING BLOCKS;Furan&Benzofuran;Aromatics Compounds;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 52490-15-0.mol

Chemical Properties

• Melting Point: 119 °C
• Boiling Point: 490.6 °C at 760 mmHg
• Flash Point: 250.5 °C
• Appearance: /
• Density: 1.183
• Vapor Pressure: 3E-10mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.69±0.15(Predicted)
• CAS DataBase Reference: 2-Butyl-3-(4-hydroxybenzoyl)benzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butyl-3-(4-hydroxybenzoyl)benzofuran(52490-15-0)
• EPA Substance Registry System: 2-Butyl-3-(4-hydroxybenzoyl)benzofuran(52490-15-0)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 52490-15-0(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C19H18O3/c1-2-3-7-17-18(15-6-4-5-8-16(15)22-17)19(21)13-9-11-14(20)12-10-13/h4-6,8-12,20H,2-3,7H2,1H3

Synthetic route

2-n-butyl 3-(4-methoxy benzoyl)-benzofuran (83790-87-8) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
aluminium chloride In 1,1-dichloroethane; water	100%
With aluminum (III) chloride In chlorobenzene at 80℃; for 2h; Inert atmosphere;	91.6%
With aluminum (III) chloride In toluene at 80 - 90℃; Solvent; Temperature; Large scale;	86.9%

2-n-butylbenzo[b]furan (4265-27-4) + 4-methoxy-benzoyl chloride (100-07-2) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -20 - -15℃; for 10h; Reflux;	92.8%
With aluminum (III) chloride In 1,2-dichloro-ethane at -10 - 60℃; for 7h; Temperature;	92%
With aluminum (III) chloride In 1,2-dichloro-ethane at -20 - -10℃; for 10h; Reflux; Large scale;	40.1%
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 2: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

phosgene (75-44-5) + 2-n-butylbenzo[b]furan (4265-27-4) + 1,1-dichloroethane (75-34-3) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
With sodium hydrogencarbonate; aluminium chloride In water; methoxybenzene	70%

4-methoxy-benzoyl chloride (100-07-2) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: carbon disulfide / 0.5 h / Inert atmosphere; Cooling with ice 1.2: 75 h / 0 - 20 °C 2.1: sodium thioethylate / N,N-dimethyl-formamide / 16 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: aluminum (III) chloride / chlorobenzene / 2 h / 80 °C / Inert atmosphere View Scheme

2-n-butylbenzo[b]furan (4265-27-4) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: carbon disulfide / 0.5 h / Inert atmosphere; Cooling with ice 1.2: 75 h / 0 - 20 °C 2.1: sodium thioethylate / N,N-dimethyl-formamide / 16 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 5 °C 1.2: 2 h / 5 - 25 °C 2.1: aluminum (III) chloride / toluene / 6 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: aluminum (III) chloride / chlorobenzene / 2 h / 80 °C / Inert atmosphere View Scheme

methyl 2-(2-formylphenoxy)hexanoate (138320-26-0) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / methanol / 3 h / 20 - 30 °C 1.2: 1 h 2.1: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C 3.1: triethylamine; p-toluenesulfonyl chloride / toluene / 2 h / 70 - 80 °C 3.2: 2 h / 70 - 75 °C 4.1: aluminum (III) chloride / dichloromethane / 10 h / -20 - -15 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / water / 20 - 30 °C / Large scale 2: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 3: aluminum (III) chloride / 1,2-dichloro-ethane / 10 h / -20 - -10 °C / Reflux; Large scale View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water / 20 - 30 °C / Large scale 2: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 3: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 4: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / methanol / 4 h / 20 - 30 °C / Large scale 2: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C / Large scale 3: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 4: aluminum (III) chloride / 1,2-dichloro-ethane / 10 h / -20 - -10 °C / Reflux; Large scale View Scheme
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid / methanol / 4 h / 20 - 30 °C / Large scale 2: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C / Large scale 3: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 4: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 5: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

C16H24O5 → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C 2.1: triethylamine; p-toluenesulfonyl chloride / toluene / 2 h / 70 - 80 °C 2.2: 2 h / 70 - 75 °C 3.1: aluminum (III) chloride / dichloromethane / 10 h / -20 - -15 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C / Large scale 2: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 3: aluminum (III) chloride / 1,2-dichloro-ethane / 10 h / -20 - -10 °C / Reflux; Large scale View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C / Large scale 2: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 3: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 4: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

2-(2-formyl-phenoxy)-hexanoic acid (138320-27-1) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; p-toluenesulfonyl chloride / toluene / 2 h / 70 - 80 °C 1.2: 2 h / 70 - 75 °C 2.1: aluminum (III) chloride / dichloromethane / 10 h / -20 - -15 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 2: aluminum (III) chloride / 1,2-dichloro-ethane / 10 h / -20 - -10 °C / Reflux; Large scale View Scheme
Multi-step reaction with 3 steps 1: acetic anhydride; sodium acetate / 90 - 100 °C / Large scale 2: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 3: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

methyl 2-bromohexanoate (5445-19-2) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; toluene / 0.5 h / 60 - 70 °C 1.2: 2 h / 80 - 100 °C 2.1: toluene-4-sulfonic acid / methanol / 3 h / 20 - 30 °C 2.2: 1 h 3.1: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C 4.1: triethylamine; p-toluenesulfonyl chloride / toluene / 2 h / 70 - 80 °C 4.2: 2 h / 70 - 75 °C 5.1: aluminum (III) chloride / dichloromethane / 10 h / -20 - -15 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: caesium carbonate; Aliquat 336 / ethyl acetate / 8 h / 80 °C / Large scale 1.2: 5 h / Reflux; Large scale 2.1: aluminum (III) chloride / 1,2-dichloro-ethane / 10 h / -20 - -10 °C / Reflux; Large scale View Scheme
Multi-step reaction with 3 steps 1.1: caesium carbonate; Aliquat 336 / ethyl acetate / 8 h / 80 °C / Large scale 1.2: 5 h / Reflux; Large scale 2.1: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 3.1: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

salicylaldehyde (90-02-8) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide; toluene / 0.5 h / 60 - 70 °C 1.2: 2 h / 80 - 100 °C 2.1: toluene-4-sulfonic acid / methanol / 3 h / 20 - 30 °C 2.2: 1 h 3.1: sodium hydroxide / toluene; water / 4 h / 35 - 40 °C 4.1: triethylamine; p-toluenesulfonyl chloride / toluene / 2 h / 70 - 80 °C 4.2: 2 h / 70 - 75 °C 5.1: aluminum (III) chloride / dichloromethane / 10 h / -20 - -15 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: caesium carbonate; Aliquat 336 / ethyl acetate / 8 h / 80 °C / Large scale 1.2: 5 h / Reflux; Large scale 2.1: aluminum (III) chloride / 1,2-dichloro-ethane / 10 h / -20 - -10 °C / Reflux; Large scale View Scheme
Multi-step reaction with 3 steps 1.1: caesium carbonate; Aliquat 336 / ethyl acetate / 8 h / 80 °C / Large scale 1.2: 5 h / Reflux; Large scale 2.1: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 3.1: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

4-methoxybenzoic acid (100-09-4) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 75 - 85 °C / Large scale 2: aluminum (III) chloride / 1,2-dichloro-ethane / 10 h / -20 - -10 °C / Reflux; Large scale View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / toluene / 75 - 85 °C / Large scale 2: aluminum (III) chloride / 1,2-dichloro-ethane / -20 - -10 °C / Large scale 3: aluminum (III) chloride / toluene / 80 - 90 °C / Large scale View Scheme

1-(4-methoxyphenyl)-1,3-heptanedione (1137261-90-5) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C 2: boron tribromide / dichloromethane View Scheme

1-(4-methoxyphenyl)ethanone (100-06-1) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / mineral oil; tetrahydrofuran / Reflux 2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C 3: boron tribromide / dichloromethane View Scheme

methyl valerate (624-24-8) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / mineral oil; tetrahydrofuran / Reflux 2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C 3: boron tribromide / dichloromethane View Scheme

2-Iodophenol (533-58-4) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate; copper(l) iodide; tetra-(n-butyl)ammonium iodide; palladium / toluene / 40 °C / Inert atmosphere 2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 5 °C 2.2: 2 h / 5 - 25 °C 3.1: aluminum (III) chloride / toluene / 6 h / Reflux View Scheme

hex-1-yne (693-02-7) → 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate; copper(l) iodide; tetra-(n-butyl)ammonium iodide; palladium / toluene / 40 °C / Inert atmosphere 2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 5 °C 2.2: 2 h / 5 - 25 °C 3.1: aluminum (III) chloride / toluene / 6 h / Reflux View Scheme

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran (1951-26-4)

Conditions	Yield
Stage #1: 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran With iodine; potassium carbonate In methanol; water at 40 - 65℃; Stage #2: With hydrogenchloride; sodium sulfite In methanol; water at 20 - 30℃; for 2h; pH=1 - 2; pH-value;	98.8%
With iodine; sodium hydroxide In methanol at 0 - 20℃; for 3h;	72%
With iodine; iodic acid In acetic acid
With hydrogenchloride; sodium hydroxide; iodine In methanol	0.914 g (47%)
With iodine; potassium carbonate In ethanol for 2h; Reflux;	14.61 g

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → (2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

Conditions	Yield
With aluminum (III) chloride In chlorobenzene at 80℃; for 2h; Inert atmosphere;	91.9%

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 4-(2-butylbenzofuran-3-carbonyl)phenyl sulfurofluoridate

Conditions	Yield
With potassium fluoride; triethylamine; N,N`-sulfuryldiimidazole; trifluoroacetic acid In dichloromethane at 20℃; for 16h; Sealed tube;	91%
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; Sealed tube;	89%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → Dideiodoamiodarone

Conditions	Yield
With potassium carbonate; sodium iodide In water; toluene at 20℃;	88%

benzyl-(2-chloro-ethyl)-ethyl-amine (60154-59-8) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → {4-[2-(benzyl-ethyl-amino)-ethoxy]-phenyl}-(2-butyl-benzofuran-3-yl)-methanone (1096359-57-7)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 20℃; for 24h;	85%

pivaloyl chloride (3282-30-2) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 4-(2-butylbenzofuran-3-carbonyl)phenyl pivalate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Sealed tube;	83%

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) + ethylene dibromide (106-93-4) → 2-n-butyl-3-[4-(2-bromo-ethoxy)-benzoyl]-benzofuran

Conditions	Yield
With potassium carbonate In chloroform; butanone	72.6%

2-(tert-butoxycarbonylamino)ethyl methanesulfonate (96628-67-0) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → {2-[4-(2-butyl-benzofuran-3-carbonyl)-phenoxy]-ethyl}-carbamic acid tert-butyl ester (1096359-54-4)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 50℃;	68%

sodium sulfate (7757-82-6) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) + ethylene dibromide (106-93-4) → 2-n-butyl-3-[4-(2-bromo-ethoxy)-benzoyl]-benzofuran

Conditions	Yield
With sodium hydroxide; potassium carbonate In diethyl ether; butanone	60%

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → (2-butyl-benzofuran-3-yl)-(3,5-dibromo-4-hydroxy-phenyl)-methanone

Conditions	Yield
With N-Bromosuccinimide In dichloromethane; N,N-dimethyl-formamide at -10 - 20℃; for 17h;	44%
With bromine In acetic acid-water; acetic acid

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 2-n-butyl-3-(3-iodo-4-hydroxybenzoyl)-benzofuran + 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran (1951-26-4)

Conditions	Yield
With potassium hydroxide; sodium hypochlorite; sodium iodide In methanol at -5℃; for 4h;	A 25% B 11%

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) + 2-(diethylamino)ethyl chloride (100-35-6) → Dideiodoamiodarone

Conditions	Yield
With sodium ethanolate

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 2-n-butyl-3-(3-iodo-4-hydroxybenzoyl)-benzofuran

Conditions	Yield
With iodine; iodic acid In acetic acid

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → Didesethylamiodarone

Conditions	Yield
Multi-step reaction with 2 steps 1: I2; HIO3 / acetic acid 2: sodium ethoxide View Scheme

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → Deiodoamiodarone

Conditions	Yield
Multi-step reaction with 2 steps 1: I2; HIO3 / acetic acid 2: sodium ethoxide View Scheme

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → (2-butylbenzofuran-3-yl)-[4-ethoxy-3,5-diiodophenyl]-methanone

Conditions	Yield
Multi-step reaction with 2 steps 1: I2; HIO3 / acetic acid View Scheme

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → (2-butylbenzofuran-3-yl)-[4-(2-hydroxyethoxy)-3,5-diiodophenyl]-methanone

Conditions	Yield
Multi-step reaction with 2 steps 1: I2; HIO3 / acetic acid View Scheme

phosphoric acid (86119-84-8, 7664-38-2) + 4-chlorosulfonyl-2-hydroxy-benzoic acid (98273-15-5) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 4-[4-(2-Butyl-benzofuran-3-carbonyl)-phenoxysulfonyl]-2-hydroxy-benzoic acid

Conditions	Yield
	0.185 g (11%)

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 4-[(2-butyl-benzofuran-3-yl)-hydroxy-methyl]-phenol

Conditions	Yield
In tetrahydrofuran

tritylaminoethyl chloride + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → triphenylmethyl alcohol (76-84-6)

Conditions	Yield
In methanol; water; acetic acid; N,N-dimethyl-formamide

calcium hypochlorite (7778-54-3) + aqueous potassium hypochlorite + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 2-n-butyl-3-(3',5'-dichloro-4'-hydroxybenzoyl)benzofuran

Conditions	Yield
With hydrogenchloride; potassium hydroxide; sodium hydroxide; potassium carbonate In methanol; water

2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → 2-n-butyl-3-[4'-(2,3-epoxy)propoxybenzoyl]benzofuran (55877-12-8) + 2-n-butyl-3-[4'-(2-hydroxy-3-chloro)propoxybenzoyl]benzofuran

Conditions	Yield
With sodium hydroxide; sodium chloride In water

1-hydroxy-6-amino-3-naphthalenesulfonic acid (87-02-5) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → C29H24N2O7S

Conditions	Yield
Stage #1: 7-amino-4-hydroxy-2-naphthalenesulfonic acid With hydrogenchloride; sodium nitrite at 0 - 5℃; for 0.5h; Stage #2: 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran With sodium hydroxide at 0 - 20℃; for 2.5h; pH=2 - 3;

5-amino-4-hydroxy-naphthalene-1,7-disulfonic acid (6483-81-4) + 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran (52490-15-0) → C29H24N2O10S2 (1427182-24-8)

Conditions	Yield
Stage #1: 5-amino-4-hydroxy-naphthalene-1,7-disulfonic acid With hydrogenchloride; sodium nitrite at 0 - 5℃; for 0.5h; Stage #2: 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran With sodium hydroxide at 0 - 20℃; for 2.5h; pH=2 - 3;

Upstream product

• 75-44-5 phosgene 
• 4265-27-4 2-n-butylbenzo[b]furan 
• 75-34-3 1,1-dichloroethane 
• 693-02-7 hex-1-yne 
• 533-58-4 2-Iodophenol 
• 624-24-8 methyl valerate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1137261-90-5 1-(4-methoxyphenyl)-1,3-heptanedione 
• 100-09-4 4-methoxybenzoic acid 
• 90-02-8 salicylaldehyde 
• 5445-19-2 methyl 2-bromohexanoate 
• 138320-27-1 2-(2-formyl-phenoxy)-hexanoic acid 
• 138320-26-0 methyl 2-(2-formylphenoxy)hexanoate 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 147030-50-0 2-n-butyl-3-(3-iodo-4-hydroxybenzoyl)-benzofuran 
• 1951-26-4 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran 
• 1096359-54-4 {2-[4-(2-butyl-benzofuran-3-carbonyl)-phenoxy]-ethyl}-carbamic acid tert-butyl ester 
• 23551-25-9 Dideiodoamiodarone 
• 1096359-57-7 {4-[2-(benzyl-ethyl-amino)-ethoxy]-phenyl}-(2-butyl-benzofuran-3-yl)-methanone 
• 76-84-6 triphenylmethyl alcohol 
• 85642-08-6 Deiodoamiodarone 
• 94317-95-0 Didesethylamiodarone 

Relevant articles and documents

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Preparation method of amiodarone hydrochloride

The invention relates to a preparation method of amiodarone hydrochloride. According to the preparation method, synthesis of intermediate 2-butylbenzofuran is realized under effect of a catalyst, a cocatalyst, and an acid binding agent, through Sonogashira coupling cyclization reaction of 2-iodo phenol and 1-acetylene in an organic solvent at a 2-iodo phenol to 1-acetylene molar ratio of 1:09-1.3,wherein reaction temperature ranges from 30 to 60 DEG C, and reaction time ranges from 12 to 38h. Compared with the prior art, the advantages are that: operation is simplified; operation convenienceand product stability are improved; controlling of the ratio of the catalyst to the materials is capable of increasing the purities and yields of intermediates; no column chromatography purifying is needed; cost is reduced; production efficiency is increased at the same time; and convenience is provided for industrial large scale production.

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.

Preparation method of amiodarone hydrochloride intermittent

The invention belongs to the field of medicine synthesis, and relates to a preparation method of an amiodarone hydrochloride intermittent. The method is characterized by including the following stepsthat 1, under an alkaline condition, in the presence of a phase transfer catalyst, a compound 1 and a compound 2 are subjected to nucleophilic substitution reaction to obtain a compound 3; 2, under analkaline condition, the compound 3 is hydrolyzed to generate a compound 4; 3, the compound 4 is subjected to intramolecular aldol condensation, decarboxylation and dehydration to obtain a compound 5;4, a compound 6 and thionyl chloride are subjected to heating reaction to obtain a compound 7; 5, under the presence of lewis acid, the compound 5 and the compound 7 are subjected to friede-crafts acylation reaction to obtain a compound 8; 6, under the presence of lewis acid, the compound 8 is subjected to demethylation to generate a compound 9, namely the amiodarone hydrochloride intermittent 2-butyl-3-(4-hydroxybenzoyl)benzofuran. The preparation method of the amiodarone hydrochloride intermittent has the advantages of being short in reaction time, high in product purity and high in yield,and the amiodarone hydrochloride intermittent is suitable for large-scale industrial production.

Synthesis method of 2-butyl-3-(4-hydroxybenzoyl) benzofuran

The invention discloses a synthesis method of 2-butyl-3-(4-hydroxybenzoyl) benzofuran. The synthesis method comprises the following steps: performing Friedel-Crafts acylation on 2-butylbenzofuran usedas a main raw material and p-anisoyl chloride, and directly demethylating a product in reaction fluid at the end of the Friedel-Crafts reaction without separation, thus obtaining the 2-butyl-3-(4-hydroxybenzoyl) benzofuran. The operation is simplified, and a relatively small amount of wastewater is produced. The reaction process is the 'one-pot method'; and two steps of reaction are completed byone step, so that the middle operation is eliminated, and discharging of waste water, waste gas and waste residues is reduced. According to the synthesis method, the Friedel-Crafts reaction and the hydrolysis reaction are completed by only one lewis acid, so that the number of material varieties is reduced, and the operation efficiency is improved. No prohibited chemical such as phosgene is used in the synthesis method; no carbon disulfide is used either, so as to avoid odor; air is not required to be purified, so that the production cost is reduced; and in a word, the synthesis method disclosed by the invention has the following characteristics of mild reaction conditions, simple technological operation, environmental friendliness, low cost and high yield.

Amiodarone hydrochloride preparation method

The invention belongs to the field of medicine, and especially relates to an amiodarone hydrochloride preparation method. The method takes 2-hydroxybenzaldehyde and 2-alkyl halohexoic acid ester as the raw materials to prepare 2-butylbenzofuran, 2-butylbenzofuran is taken as the raw material, and is subjected to the steps of friedel-crafts acylation, demethylation, iodination, etherification and salt forming to obtain the amiodarone hydrochloride. By employing the method, the raw materials have the advantages of low cost and easy acquisition, the process is simple, and 2-butylbenzofuran and amiodarone hydrochloride with high purity and high yield can be obtained, the cost is low, the waste water is little, and the method is suitable for industrial production.

A 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran preparation method (by machine translation)

The invention discloses a 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran of the preparation method, the preparation method comprises the following steps: (1) the 1 - (4 - methoxyphenyl) - 1, 3 - heptyl diketone, acrolein dimer, halogenated reagent and acid catalyst in organic solvent for 25 - 100 °C stirring reaction for 1 - 8 hours, to obtain the 2 - butyl - 3 - (4 - anisoyl) benzofuran; (2) the 2 - butyl - 3 - (4 - anisoyl) benzofuran is dispersed in the organic solvent containing the acid catalyst used in the 0 - 100 °C stirring for 1 - 8 hours, to obtain the 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran. The invention through the key process for the preparation of the overall process, and each reaction step of optimizing the parameter condition and the like, with the traditional 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran existing synthesis method, with a route good economic performance, high reaction selectivity, industrial application value is large and the like. (by machine translation)

DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION

A compound represented by the general Formula (I): a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A - K are individually selected from carbon or nitrogen; X = -O, -NR1,or -S; R1-11 are individually selected from the group consisting of-H, C1-C6 alkyl, C6-C aryl, substituted C6-C14 aryl, C1-C14-alkoxy, halogen, hydroxyl, carboxy, cyano, C1-C6-alkanoyloxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, trifluoromethyl, hydroxy, C2-C6-alkoxycarbonyl, C2-C6-alkanoylamino, -O-R12, S-R12,-SO2-Ri2, -NHSO2R12 and -NHCO2R12, wherein R12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C1-C6-alkyl, C6-C10 aryl,C1-C6-alkoxy and halogen, and C4-C20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.

Process for the preparation of 3-benzoyl benzofuran derivatives

The invention relates to a process for the preparation of 3-benzoyl benzofuran derivatives of general formula: STR1 wherein a benzofuran derivative of general formula: STR2 is reacted in situ in the presence of aluminium chloride successively with phosgene or oxalyl chloride, and then with a phenolic derivative of general formula: STR3 to produce a complex which is hydrolysed to form the desired compound of 3-benzoyl benzofuran.