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CAS No.: | 915095-87-3 |
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Name: | (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C17H14ClIO3 |
Molecular Weight: | 428.654 |
Synonyms: | (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone;Methanone, (2-chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]-;(S)-(2-chloro-5-iodophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone |
Density: | 1.639 |
Boiling Point: | 526℃ |
Flash Point: | 272℃ |
PSA: | 35.53000 |
LogP: | 4.34330 |
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
(S)-3-hydroxytetyrahydrofurane
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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With potassium tert-butylate In tetrahydrofuran at 16 - 25℃; for 3h; | 91.8% |
Stage #1: (2-chloro-5-iodophenyl)(4-fluorophenyl)methanone; (S)-3-hydroxytetyrahydrofurane With potassium tert-butylate In tetrahydrofuran at 16 - 25℃; for 4h; Stage #2: With water at 20 - 21℃; for 1.83333h; | 91.8% |
With potassium tert-butylate In tetrahydrofuran at 16 - 25℃; for 4h; Industry scale; | 91.8% |
(2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone
(R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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With potassium carbonate; potassium iodide In acetonitrile at 50 - 55℃; | 87% |
2-chloro-5-iodobenzoic acid
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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Stage #1: 2-chloro-5-iodobenzoic acid With oxalyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 4h; Friedel-Crafts Acylation; Stage #2: (S)-3-phenoxytetrahydrofuran With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3h; | 81% |
fluorobenzene
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 2: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 1.2: 6 h / 20 - 30 °C 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 2.2: 1.83 h / 20 - 21 °C View Scheme | |
Multi-step reaction with 2 steps 1: oxalyl dichloride; aluminum (III) chloride / N,N-dimethyl-formamide / 25 - 45 °C / Industry scale 2: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h 1.2: 1 h / 0 - 5 °C 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 16 - 25 °C View Scheme |
2-chloro-5-iodobenzoic acid
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 2: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 1.2: 6 h / 20 - 30 °C 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 2.2: 1.83 h / 20 - 21 °C View Scheme | |
Multi-step reaction with 2 steps 1: oxalyl dichloride; aluminum (III) chloride / N,N-dimethyl-formamide / 25 - 45 °C / Industry scale 2: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale View Scheme |
2-chloro-5-iodobenzoylchloride
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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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 / 6 h / -5 °C 2: potassium tert-butylate / tetrahydrofuran / 20 °C View Scheme |
phenol
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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Multi-step reaction with 2 steps 1: polyposphoric acid / 50 - 85 °C 2: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C View Scheme |
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In toluene at 0 - 23℃; for 2.5h; | 93% |
With aluminum (III) chloride; sodium tetrahydroborate In tetrahydrofuran for 5h; Reflux; | 90% |
With potassium borohydride; trifluoroacetic acid In tetrahydrofuran at 0 - 20℃; for 0.5h; | 85% |
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 1,1,3,3-Tetramethyldisiloxane / aluminum (III) chloride / toluene / 2.5 h / 18 - 26 °C 2: TurboGrignard / tetrahydrofuran / 1.83 h / -15 - 21 °C View Scheme |
(S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone
empagliflozin
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C 2.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.83 h / -21 - -15 °C 2.2: 2.92 h / -25 - -13 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C / Industry scale 1.2: 20 - 51 °C / Industry scale 2.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.83 h / -21 - -15 °C / Industry scale 2.2: 2.92 h / -25 - -18 °C / Industry scale 2.3: -13 - 19 °C / Industry scale View Scheme | |
Multi-step reaction with 5 steps 1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C 2: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.5 h / -20 - 10 °C 3: hydrogenchloride / isopropyl alcohol / 5 h / 38 - 42 °C / pH 2 4: hydrogenchloride / isopropyl alcohol; methanol 5: aluminum (III) chloride; triethylsilane / dichloromethane; acetonitrile / 0.5 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / ethanol / 20 - 25 °C 2: methanesulfonic acid / 20 - 30 °C 3: n-butyllithium / tetrahydrofuran; hexane / -75 - -70 °C / Inert atmosphere 4: methanesulfonic acid / 20 - 25 °C 5: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -40 - 20 °C / Inert atmosphere View Scheme | |
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 |