915095-84-0

Basic information

• Product Name: (S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone
• Synonyms: (S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone;(5-Bromo-2-chlorophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone
• CAS NO: 915095-84-0
• Molecular Formula: C₁₇H₁₄BrClO₃
• Molecular Weight: 381.64826
• Mol File: 915095-84-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 505.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.493±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone(915095-84-0)
• EPA Substance Registry System: (S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone(915095-84-0)

Safety Data

• Hazardous Substances Data: 915095-84-0(Hazardous Substances Data)

Usage

General Description

The chemical compound "(S)-(5-bromo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone" is a synthetic organic compound with a complex molecular structure. It contains a combination of bromo and chloro groups on a phenyl ring, as well as a tetrahydrofuran-3-yloxy group attached to another phenyl ring. (S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone is categorized as a methanone derivative and is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and materials. It has potential applications in medicinal chemistry and drug discovery due to its unique structure and reactivity. Further research and analysis are needed to fully understand the properties and potential uses of this chemical compound.

Synthetic route

(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone (915095-85-1) + (S)-3-hydroxytetyrahydrofurane (86087-23-2) → (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃;	93%
With potassium tert-butylate In tetrahydrofuran at 7 - 10℃; for 0.5h;	87%
With potassium tert-butylate In tetrahydrofuran at 0 - 10℃; for 2h;	85.3%

(5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone (1360568-68-8) + R-3-chloro-tetrahydrofuran → (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 50 - 55℃;	91%

5-bromo-2-chlorobenzoic acid (21739-92-4) → (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / fluorobenzene / 2 h / 15 - 25 °C 2: aluminum (III) chloride / 1 h / 0 - 25 °C 3: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C View Scheme
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / fluorobenzene / 15 - 25 °C / Inert atmosphere 2: aluminum (III) chloride / 25 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 2 - 10 °C View Scheme
Multi-step reaction with 2 steps 1: polyphosphoric acid / 50 - 85 °C 2: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C View Scheme

5-bromo-2-chloro-benzoyl chloride (21900-52-7) → (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1 h / 0 - 25 °C 2: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 25 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 2 - 10 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 5 h / 0 - 20 °C 2: potassium tert-butylate / tetrahydrofuran / 2 h / 0 - 10 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 8 h / 0 - 10 °C 2: 18-crown-6 ether; sodium hydroxide / toluene; water / 8 h / 50 - 60 °C View Scheme

phenol (108-95-2) → (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid / 50 - 85 °C 2: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C View Scheme

fluorobenzene (462-06-6) → (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 0 - 25 °C 1.2: 25 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene (915095-89-5)

Conditions	Yield
With aluminum (III) chloride; hydrogen In toluene at 20 - 25℃; for 3h; Temperature;	95%
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In toluene at 0 - 23℃; for 2.5h;	92%
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In toluene at 0 - 23℃;	91.28%

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C17H16BrClO3

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20 - 25℃;	98 g

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C20H24BrClO3Si

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 20 - 25 °C 2: triethylamine / dichloromethane / 0 - 35 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C18H18BrClO3

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 20 - 25 °C 2: methanesulfonic acid / 20 - 30 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C38H67ClO9Si5

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol / 20 - 25 °C 2: triethylamine / dichloromethane / 0 - 35 °C 3: n-butyllithium / tetrahydrofuran; hexane / -75 - -70 °C / Inert atmosphere View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C25H31ClO9

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / ethanol / 20 - 25 °C 2: triethylamine / dichloromethane / 0 - 35 °C 3: n-butyllithium / tetrahydrofuran; hexane / -75 - -70 °C / Inert atmosphere 4: methanesulfonic acid / 0 - 35 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → empagliflozin (864070-44-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / ethanol / 20 - 25 °C 2: triethylamine / dichloromethane / 0 - 35 °C 3: n-butyllithium / tetrahydrofuran; hexane / -75 - -70 °C / Inert atmosphere 4: methanesulfonic acid / 0 - 35 °C 5: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -40 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium borohydride; aluminium trichloride / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / -10 - 0 °C / Cooling with ice; Inert atmosphere 2.3: 40 - 50 °C / Inert atmosphere 3.1: lithium hydroxide / ethanol; water / 40 - 45 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium borohydride; aluminium trichloride / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / 0.5 h / -10 - 0 °C / Cooling with ice; Inert atmosphere 2.2: 40 - 50 °C / Inert atmosphere 3.1: potassium carbonate / tetrahydrofuran / 40 - 45 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium borohydride; aluminium trichloride / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / 0.5 h / -10 - 0 °C / Cooling with ice; Inert atmosphere 2.2: 40 - 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / toluene; tetrahydrofuran; hexane / 0.5 h / -80 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 1.3: 12 h / 30 °C / Inert atmosphere 2.1: 4-methyl-morpholine; dmap / ethyl acetate / 4 h / 5 - 30 °C / Inert atmosphere; Large scale 3.1: phenylsilane; aluminum (III) chloride / acetonitrile / 6 h / 45 °C / Inert atmosphere; Large scale View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride; potassium borohydride / tetrahydrofuran / 6 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 8 h / 8 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium dihydrogenphosphate / toluene / 12 h / 105 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C43H59ClO11

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium borohydride; aluminium trichloride / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.1: TurboGrignard / tetrahydrofuran / -10 - 0 °C / Cooling with ice; Inert atmosphere 2.3: 40 - 50 °C / Inert atmosphere View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → (4-chloro-3-(4-(3(S)-tetrahydrofuranyloxy)benzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanone

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 24.5 h / 0 - 60 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -80 - -70 °C 2.2: -80 - 0 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → (4-chloro-3-(4-(3(S)-tetrahydrofuryloxy)benzyl)phenyl)((3aS,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 24.5 h / 0 - 60 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -80 - -70 °C 2.2: -80 - 0 °C 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -80 - 70 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C30H33ClO11

Conditions	Yield
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 24.5 h / 0 - 60 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -80 - -70 °C 2.2: -80 - 0 °C 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -80 - 70 °C 4.1: acetic acid / water / 100 °C 4.2: 5 h / 0 - 30 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C29H32BrClO9

Conditions

Yield

Multi-step reaction with 5 steps 1.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 24.5 h / 0 - 60 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -80 - -70 °C 2.2: -80 - 0 °C 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -80 - 70 °C 4.1: acetic acid / water / 100 °C 4.2: 5 h / 0 - 30 °C 5.1: potassium fluoride; trimethylsilyl trifluoromethanesulfonate / acetonitrile / -80 - -70 °C View Scheme

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → C32H35ClO13

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; tetrahydrofuran; hexane / 0.5 h / -80 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 1.3: 12 h / 30 °C / Inert atmosphere 2.1: 4-methyl-morpholine; dmap / ethyl acetate / 4 h / 5 - 30 °C / Inert atmosphere; Large scale View Scheme

methanol (67-56-1) + (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) + (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9) → [2-chloro-5-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2 methoxy-tetrahydropyran-2-yl]phenyl]-[4-[(3S)-tetrahydrofuran-3-yl]oxyphenyl]methanone

Conditions

Yield

Stage #1: (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone With n-butyllithium In tetrahydrofuran; hexane; toluene at -80℃; for 0.5h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene for 2h; Inert atmosphere; Stage #3: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 30℃; for 12h; Inert atmosphere;

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-84-0) → 2-[4-chloro-3-({4-[(3S)-oxolan-3-yloxy]phenyl}methyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride; potassium borohydride / tetrahydrofuran / 6 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 8 h / 8 °C / Inert atmosphere View Scheme

Upstream product

• 17696-62-7 Phenyl 4-hydroxybenzoate 
• 25804-49-3 tert-butyl 4-hydroxybenzoate 
• 27522-79-8 p-hydroxybenzoylethylamine 
• 106-39-8 bromochlorobenzene 
• 462-06-6 fluorobenzene 
• 108-95-2 phenol 
• 1360568-68-8 (5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 915095-85-1 (5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone 
• 86087-23-2 (S)-3-hydroxytetyrahydrofurane 

Downstream Products

• 915095-99-7 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate 
• 864070-44-0 empagliflozin 
• 915095-89-5 (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene 

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