864070-18-8

Basic information

• Product Name: 4-(5-broMo-2-chlorobenzyl)phenol
• Synonyms: 4-(5-broMo-2-chlorobenzyl)phenol;4-[(5-bromo-2-chlorophenyl)methyl]-Phenol;Phenol, 4-[(5-bromo-2-chlorophenyl)methyl]-
• CAS NO: 864070-18-8
• Molecular Formula: C₁₃H₁₀BrClO
• Molecular Weight: 297.5749
• EINECS: 1592732-453-0
• Mol File: 864070-18-8.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 401.3±35.0 °C(Predicted)
• Appearance: /
• Density: 1.522±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.14±0.15(Predicted)
• CAS DataBase Reference: 4-(5-broMo-2-chlorobenzyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-broMo-2-chlorobenzyl)phenol(864070-18-8)
• EPA Substance Registry System: 4-(5-broMo-2-chlorobenzyl)phenol(864070-18-8)

Safety Data

• Hazardous Substances Data: 864070-18-8(Hazardous Substances Data)

Usage

Uses

4-(5-Bromo-2-chlorobenzyl)phenol can be used to treat diabetes or any related diseases.

Synthetic route

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene (461432-23-5) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
With boron tribromide; sodium hydrogencarbonate In dichloromethane at 20 - 30℃; for 0.5h; Inert atmosphere;	100%
Stage #1: 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene With boron trichloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With boron tribromide In dichloromethane at 0℃;	98%
With boron tribromide In dichloromethane for 1h;	95%

4-bromo-1-chloro-2-(4-methoxybenzyl)benzene → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Stage #1: 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene With boron tribromide In dichloromethane at 20℃; for 2h; Stage #2: With potassium carbonate In dichloromethane; water at 20℃; Stage #3: With hydrogenchloride In dichloromethane; water pH=1;	98%
Stage #1: 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene With boron tribromide In dichloromethane at 0 - 20℃; for 2h; Stage #2: With potassium carbonate In dichloromethane at 0℃; Stage #3: With hydrogenchloride In dichloromethane; water at 20℃; pH=1;	98%
Stage #1: 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene With boron tribromide In dichloromethane at 0 - 20℃; for 2h; Stage #2: With water; potassium carbonate In dichloromethane at 0℃;	98%

(5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone (1360568-68-8) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
With triethylsilane; boron trifluoride diethyl etherate In diethyl ether; dichloromethane; acetonitrile at 20℃; for 16h; Inert atmosphere;	94.8%

5-bromo-2-chlorobenzoic acid (21739-92-4) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 20 °C 2: aluminum (III) chloride / dichloromethane / 1 h / -5 - 0 °C 3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C 4: boron tribromide / dichloromethane / 25 h / -78 - 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 10 h / 20 °C 2.1: aluminum (III) chloride / dichloromethane / 1 h / -5 - 20 °C / Inert atmosphere 2.2: 2 h / -5 - 0 °C / Inert atmosphere 3.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 18 h / 5 - 20 °C / Inert atmosphere 4.1: boron tribromide / dichloromethane / -10 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C 2.1: aluminum (III) chloride / dichloromethane / 0.33 h / -5 °C / Inert atmosphere 2.2: 3 h / -5 °C / Inert atmosphere 3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2.33 h / 0 - 20 °C / Inert atmosphere 4.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere; Darkness View Scheme

phenol (108-95-2) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 0.5 h / 20 °C 1.2: 3 h / Reflux 2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C 3.1: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 4.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 16 h / 20 °C / Inert atmosphere View Scheme

5-bromo-2-chloro-benzoyl chloride (21900-52-7) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 1 h / -5 - 0 °C 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C 3: boron tribromide / dichloromethane / 25 h / -78 - 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / dichloromethane / 1 h / -5 - 20 °C / Inert atmosphere 1.2: 2 h / -5 - 0 °C / Inert atmosphere 2.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 18 h / 5 - 20 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / -10 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / dichloromethane / 0.33 h / -5 °C / Inert atmosphere 1.2: 3 h / -5 °C / Inert atmosphere 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2.33 h / 0 - 20 °C / Inert atmosphere 3.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere; Darkness View Scheme

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone (461432-22-4) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -20 - 20 °C 2: boron tribromide / dichloromethane / 25 h / -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: triethylsilane / acetonitrile / 10 - 15 °C 1.2: 10 - 45 °C 2.1: boron tribromide / dichloromethane / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 5 - 10 °C 2: boron tribromide / dichloromethane / 1 h View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 2: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 16 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylsilane; trifluorormethanesulfonic acid; trifluoroacetic acid / 20 °C / Reflux 2: boron tribromide / dichloromethane / -78 - 20 °C View Scheme

Phenetole (103-73-1) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h 1.2: 1 h / 4 - 5 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 5 - 10 °C 3.1: boron tribromide / dichloromethane / 1 h View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C 2: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 3: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 16 h / 20 °C / Inert atmosphere View Scheme

(5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone (333361-49-2) → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 18 h / 5 - 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / -10 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2.33 h / 0 - 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere; Darkness View Scheme
Multi-step reaction with 2 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 2.33 h / 0 - 20 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere; Darkness View Scheme

C20H13BrClNO4 → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; ethanol / 0 - 5 °C 2: 0.5 h 3: hydrogen; palladium on activated charcoal / methanol View Scheme

C20H15BrClNO4 → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h 2: hydrogen; palladium on activated charcoal / methanol View Scheme

C22H17BrClNO5 → 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol	2.5 g

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + tert-butyldimethylsilyl chloride (18162-48-6) → [4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silane (864070-19-9)

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0℃;	99%
With 1H-imidazole In dichloromethane at 25 - 35℃;	97.54%
With triethylamine In dichloromethane at 20℃; for 15h;	97.7%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + d(4)-methanol (811-98-3) → 4-bromo-1-chloro-2-(4-(methoxy-d3)benzyl)benzene (1204219-82-8)

Conditions	Yield
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 30℃; for 0.5h; Stage #2: d(4)-methanol In tetrahydrofuran at 30℃;	99%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + ethyl iodide (75-03-6) → 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene (461432-23-5)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 20℃;	96%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + 2-(2,2-difluoroethoxy)ethyl-4-methylbenzenesulfonate (1118567-13-7) → 4-bromo-1-chloro-2-(4-(2-(2,2-difluoroethoxy)ethoxy)benzyl)benzene (1204221-35-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	91.9%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + methyl-d3 4-methylbenzenesulfonate (7575-93-1) → 4-bromo-1-chloro-2-(4-(methoxy-d3)benzyl)benzene (1204219-82-8)

Conditions	Yield
With potassium carbonate In acetone at 80℃; for 16h;	91%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + ethanol-d6 (1516-08-1) → 4-bromo-1-chloro-2-(4-(ethoxy-d5)benzyl)benzene (1204219-73-7)

Conditions	Yield
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 30℃; for 0.5h; Stage #2: ethanol-d6 In tetrahydrofuran at 30℃;	90%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + chloromethyl methyl ether (107-30-2) → 4-bromo-1-chloro-2-(4-(methoxymethoxy)benzyl)-benzene

Conditions	Yield
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;	90%
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;	90%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + allyl bromide (106-95-6) → 2-(4-(allyloxy)benzyl)-4-bromo-1-chlorobenzene (1416165-16-6)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	89.6%
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	89.6%
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	89.6%

[1-(trifluoromethyl)cyclopropyl]methyl-4-methylbenzene-1-sulfonate (865833-72-3) + 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) → 4-bromo-1-chloro-2-(4-((1-(trifluoromethyl)cyclopropyl)methoxy)benzyl)benzene (1360569-00-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 5h; Inert atmosphere;	88%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + 2,2,2-Trifluoroethyl p-toluenesulfonate (433-06-7) → 4-bromo-1-chloro-2-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]benzene (1358581-01-7)

Conditions	Yield
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,2-Trifluoroethyl p-toluenesulfonate In N,N-dimethyl-formamide at 140℃; for 12h; Inert atmosphere;	87.2%
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h; Stage #2: 2,2,2-Trifluoroethyl p-toluenesulfonate In N,N-dimethyl-formamide	39.2%

1-bromo-2-propanol (19686-73-8) + 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) → 1-(4-(5-bromo-2-chlorobenzyl)phenoxy)propan-2-ol (1118567-32-0)

Conditions	Yield
With caesium carbonate In ISOPROPYLAMIDE at 80℃;	82%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + 2-(cyclopropyloxy)ethyl-4-methylbenzenesulfonate (862728-59-4) → 4-bromo-1-chloro-2-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]benzene (1118567-45-5)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	81%
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-(cyclopropyloxy)ethyl-4-methylbenzenesulfonate In N,N-dimethyl-formamide at 20℃;	64%
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-(cyclopropyloxy)ethyl-4-methylbenzenesulfonate In N,N-dimethyl-formamide at 20℃;	64%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + (1-(trifluoromethyl)cyclobutyl)methyl 4-methylbenzenesulfonate (1038404-00-0) → 4-bromo-1-chloro-2-(4-((1-(trifluoromethyl)cyclobutyl)methoxy)benzyl)benzene (1360568-93-9)

Conditions	Yield
In N,N-dimethyl-formamide at 110℃; for 5h; Inert atmosphere;	79.4%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + ethyl bromoacetate (105-36-2) → ethyl 2-(4-(2-chloro-5-bromobenzyl)phenoxy)acetate (1204221-60-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	78%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + (4,4-difluoro-1-methylcyclohexyl)methyl 4-methylbenzenesulfonate (1360568-92-8) → 4-bromo-1-chloro-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)benzene (1360569-03-4)

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 5h; Inert atmosphere;	77.9%

2-iodo-propane (75-30-9) + 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) → 4-bromo-1-chloro-2-(4-isopropoxybenzyl)benzene (1369406-05-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;	77%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + 2-bromoethanol (540-51-2) → 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethanol (1118566-50-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	76%
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-bromoethanol In N,N-dimethyl-formamide at 80℃;	76%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + (1-ethylcyclobutyl)methyl 4-methylbenzenesulfonate (1360568-76-8) → 4-bromo-l-chloro-2-(4-((1-ethylcyclobutyl)methoxy)benzyl)benzene (1360568-77-9)

Conditions	Yield
caesium carbonate In dichloromethane; N,N-dimethyl-formamide at 120℃;	75%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-4-(5-bromo-2-chlorobenzyl)phenyl dimethylcarbamothioate (1192136-39-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	73%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + benzyl bromide (100-39-0) → 2-[(4-benzyloxyphenyl)methyl]-4-bromo-1-chlorobenzene

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20 - 30℃; for 12h; Inert atmosphere;	70.4%
With potassium hydroxide In tetrahydrofuran at 20 - 30℃; for 12h;	70.4%
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + ethanol-1,1-d2 (1859-09-2) → 4-bromo-1-chloro-2-(4-(ethoxy-1,1-d2)benzyl)benzene (1204219-63-5)

Conditions	Yield
Stage #1: 4-(5-bromo-2-chlorobenzyl)phenol With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 30℃; for 0.5h; Stage #2: ethanol-1,1-d2 In tetrahydrofuran at 30℃;	63%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + (R)-3-Hydroxytetrahydrofuran (86087-24-3) → (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene (915095-89-5)

Conditions	Yield
Stage #1: (R)-3-Hydroxytetrahydrofuran With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: 4-(5-bromo-2-chlorobenzyl)phenol In dichloromethane at 20℃; for 20h;	55%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + (1-methylcyclopentyl)methyl 4-methylbenzenesulfonate (1360568-96-2) → 4-bromo-1-chloro-2-(4-((1-methylcyclopentyl)methoxy)benzyl)benzene (1360568-97-3)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 5h; Inert atmosphere;	53.8%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + (1R,3r,5S)-bicyclo[3.1.0]hexan-3-yl methanesulfonate (1335139-58-6) → (1R,3s,5S)-3-(4-(5-bromo-2-chlorobenzyl)phenyloxy)bicyclo[3.1.0]hexane

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; caesium carbonate In 1-methyl-pyrrolidin-2-one at 50℃;	50%
With N-benzyl-N,N,N-triethylammonium chloride; caesium carbonate In 1-methyl-pyrrolidin-2-one at 20 - 50℃;	50%
With N-benzyl-N,N,N-triethylammonium chloride; caesium carbonate In 1-methyl-pyrrolidin-2-one at 20 - 50℃;	50%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + (1R,3r,5S)-bicyclo[3.1.0]hexan-3-yl methanesulfonate (1335139-58-6) → (1R,3r,5S)-3-(4-(5-bromo-2-chlorobenzyl)phenyloxy)bicyclo[3.1.0]hexane

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 70℃; for 2h;	27%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 70℃; for 2h;	27%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 70℃; for 2h;	27%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + cyclopentyl iodide (1556-18-9) → 4-bromo-1-chloro-2-(4-cyclopentyloxy-benzyl)-benzene (915095-88-4)

Conditions	Yield
With caesium carbonate In ethanol at 60℃;

oxetan-3-yl 4-methylbenzenesulfonate (26272-83-3) + 4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) → 3-(4-(5-bromo-2-chlorobenzyl)phenoxy)oxetane (1210344-20-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 120℃;

Upstream product

• 333361-51-6 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene 
• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 108-95-2 phenol 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 461432-22-4 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone 
• 103-73-1 Phenetole 
• 1360568-68-8 (5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 

Downstream Products

• 1118566-50-9 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethanol 
• 1118567-32-0 1-(4-(5-bromo-2-chlorobenzyl)phenoxy)propan-2-ol 
• 1118567-45-5 4-bromo-1-chloro-2-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]benzene 
• 1192136-39-2 O-4-(5-bromo-2-chlorobenzyl)phenyl dimethylcarbamothioate 
• 1204220-63-2 (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1298086-14-2 methyl 1-C-[4-chloro-3-(4-{[(2, 6-dichlorophenyl)sulfonyl]oxy}benzyl)phenyl]-6-O-[(2,6-dichlorophenyl)sulfonyl]-alpha-D-glucopyranoside 
• 1298086-38-0 (2S,3R,4S,5S)-2-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-6,6-bis-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol 
• 1360569-36-3 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((1-( trifluoromethyl)cyclobutyl)methoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1360569-35-2 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((1-(trifluoromethyl)cyclobutyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1360569-37-4 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((1-methylcyclopentyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1360569-38-5 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((1-methylcyclopentyl)methoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1360569-39-6 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((1-(trifluoromethyl)cyclopropyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1360569-40-9 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((1-(trifluoromethyl)cyclopropyl)methoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1360568-85-9 3-((4-(5-bromo-2-chlorobenzyl)phenoxy)methyl)-3-ethyloxetane 

Relevant articles and documents

Synthesis method of dapagliflozin intermediate 5-bromo-2-chloro-4 '-ethoxydiphenylmethane

The invention discloses a synthesis method of a dapagliflozin intermediate 5-bromo-2-chloro-4 '-ethoxydiphenylmethane. The method comprises the following steps: using 5-bromo-2-chlorobenzoic acid as araw material to be acylated by thionyl chloride, and then carrying out acylation reaction with 1-nitro-4-(phenoxymethyl) benzene, reducing, acetylating, hydrogenating and ethylating to obtain the dapagliflozin intermediate 5-bromo-2-chloro-4'-ethoxydiphenylmethane. The method can effectively avoid the acylation reaction ortho-position by-product so that the preparation of dapagliflozin is convenient for quality control, the reaction is mild, the yield is high and the method has an industrial application prospect.

Dicyclic derivative of glucoside as well as preparation method and application of dicyclic derivative

The invention relates to a dicyclic derivative of glucoside as well as a preparation method and the application of the dicyclic derivative. Specifically, the invention relates to a compound as shown in Formula I, a stereisomer or pharmaceutically acceptable salt or ester of the compound, a pharmaceutical composition of the compound, and application of the compound in preparation of drugs for treating diabetes or relevant diseases.

Glucopyranosyl derivative and application thereof in medicine

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