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CAS No.: | 915095-94-2 |
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Name: | (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C17H16ClIO2 |
Molecular Weight: | 414.67 |
Synonyms: | 查看更多英文别名查看更多英文别名 | "> (S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran;(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan;(S)-3-(4-(2-chloro-5-iodobenzyl)phenoxy)-tetrahydrofuran;Empagliflozin Intermediate1;Empagliflozin II;Empagliflozin intermediate;
EINECS: | 619-599-0 |
Density: | 1.578±0.06 g/cm3 (20 oC 760 Torr) |
Boiling Point: | 476.0±45.0 °C(Predicted) |
PSA: | 18.46000 |
LogP: | 4.70310 |
(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% |
4-(2-chloro-5-iodobenzyl)phenol
toluene-4-sulfonic acid (S)-(tetrahydrofuran-3-yl)ester
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile at 50 - 55℃; Large scale; | 90.1% |
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Stage #1: (S)-3-(4-(5-iodo-2-aminobenzyl)phenoxy)tetrahydrofuran With hydrogenchloride; sodium nitrite In water at -10 - 0℃; for 2.5h; Stage #2: With hydrogenchloride; copper(l) chloride In water at 20 - 80℃; for 3h; | 75.2% |
fluorobenzene
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 2: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C 3: 1,1,3,3-Tetramethyldisiloxane / aluminum (III) chloride / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 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 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; aluminum (III) chloride / N,N-dimethyl-formamide / 25 - 45 °C / Industry scale 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C / Industry scale 3.2: 20 - 51 °C / Industry scale View Scheme | |
Multi-step reaction with 3 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 3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 5 - 10 °C View Scheme |
2-chloro-5-iodobenzoic acid
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 2: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C 3: 1,1,3,3-Tetramethyldisiloxane / aluminum (III) chloride / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 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 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; aluminum (III) chloride / N,N-dimethyl-formamide / 25 - 45 °C / Industry scale 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale 3.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C / Industry scale 3.2: 20 - 51 °C / Industry scale View Scheme |
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 3 h / 16 - 25 °C 2: 1,1,3,3-Tetramethyldisiloxane / aluminum (III) chloride / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 1.2: 1.83 h / 20 - 21 °C 2.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C / Industry scale 2.1: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C / Industry scale 2.2: 20 - 51 °C / Industry scale View Scheme | |
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 20 °C 2: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / 5 h / Reflux View Scheme |
2-chloro-5-iodobenzoylchloride
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Multi-step reaction with 3 steps 1: aluminum (III) chloride / 1 h / 0 - 25 °C 2: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 3: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C View Scheme | |
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 6 h / -5 °C 2: potassium tert-butylate / tetrahydrofuran / 20 °C 3: sodium tetrahydroborate; aluminum (III) chloride / tetrahydrofuran / 5 h / Reflux View Scheme |
phenol
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Multi-step reaction with 3 steps 1: polyposphoric acid / 50 - 85 °C 2: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C 3: potassium borohydride; trifluoroacetic acid / tetrahydrofuran / 0.5 h / 0 - 20 °C View Scheme |
(2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C 2: potassium borohydride; trifluoroacetic acid / tetrahydrofuran / 0.5 h / 0 - 20 °C View Scheme |
4-hydroxybenzyl chloride
(3S)-3-[4-[(2-chloro-5-iodophenyl)methyl]phenoxy]tetrahydrofuran
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: sulfonyl chloride / dichloromethane / 3 h / -5 - 0 °C 1.2: 4.5 h / Reflux 2.1: zinc(II) chloride / ethyl acetate / 6 h / Reflux 3.1: hydrogenchloride; sodium nitrite / water / 2.5 h / -10 - 0 °C 3.2: 3 h / 20 - 80 °C View Scheme |