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
• Article Data: 11

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

• 533-58-4 2-Iodophenol 
• 693-02-7 hex-1-yne 
• 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 
• 4265-27-4 2-n-butylbenzo[b]furan 
• 100-07-2 4-methoxy-benzoyl chloride 
• 75-44-5 phosgene 
• 75-34-3 1,1-dichloroethane 

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 

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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.