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CAS No.: | 915095-86-2 |
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Name: | (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C13H7ClFIO |
Molecular Weight: | 360.554 |
Synonyms: | Empagliflozin intermediate;(2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone; |
Density: | 1.752 |
Boiling Point: | 415℃ |
Flash Point: | 205℃ |
Safety: | 24/25 |
PSA: | 17.07000 |
LogP: | 4.31470 |
fluorobenzene
2-chloro-5-iodobenzoic acid
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
Conditions | Yield |
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With oxalyl dichloride; N,N-dimethyl-formamide at 25 - 30℃; for 5h; | 94% |
Stage #1: fluorobenzene; 2-chloro-5-iodobenzoic acid With oxalyl dichloride In N,N-dimethyl-formamide at 25 - 30℃; for 5h; Stage #2: With aluminum (III) chloride; water at 20 - 30℃; for 6h; | 94% |
With aluminum (III) chloride; oxalyl dichloride In N,N-dimethyl-formamide at 25 - 45℃; Industry scale; | 94% |
2-chloro-5-iodobenzoylchloride
fluorobenzene
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
Conditions | Yield |
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With aluminum (III) chloride In dichloromethane at -5℃; for 6h; | 93.4% |
Stage #1: 2-chloro-5-iodobenzoylchloride; fluorobenzene With aluminum (III) chloride at 0 - 75℃; for 1.5h; Friedel Crafts Acylation; Stage #2: With water at 0 - 25℃; | |
With aluminum (III) chloride at 0 - 25℃; for 1h; Friedel-Crafts Acylation; regioselective reaction; | 121 g |
With aluminum (III) chloride at 25℃; Inert atmosphere; | 105 g |
With aluminum (III) chloride In dichloromethane at 20℃; for 3h; Friedel-Crafts Acylation; Cooling with ice; | 42.1 g |
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
Conditions | Yield |
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Stage #1: (2-chloro-5-aminophenyl)(4-fluorophenyl)methanone With sulfuric acid; sodium nitrite In water at 0 - 10℃; Large scale; Stage #2: With urea; potassium iodide In water at 0 - 20℃; for 0.5h; Large scale; | 91.6% |
2-chloro-5-iodobenzoic acid
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
Conditions | Yield |
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Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / fluorobenzene / 2 h / 15 - 25 °C 2: aluminum (III) chloride / 1 h / 0 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2: aluminum (III) chloride / dichloromethane / 6 h / -5 °C View Scheme | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C 2: aluminum (III) chloride / dichloromethane / 3 h / 20 °C / Cooling with ice View Scheme |
ortho-chlorobenzoic acid
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
Conditions | Yield |
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Multi-step reaction with 5 steps 1.1: sulfuric acid; nitric acid / 2 h / -5 - 20 °C / Large scale 2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 25 °C / Autoclave; Reflux 3.1: aluminum (III) chloride / dichloromethane / 5 h / 0 - 5 °C / Autoclave; Large scale 4.1: iron; ammonium chloride / ethanol; water / 5 h / 78 - 80 °C / Autoclave; Large scale 5.1: sodium nitrite; sulfuric acid / water / 0 - 10 °C / Large scale 5.2: 0.5 h / 0 - 20 °C / Large scale View Scheme |
2-chloro-5-nitrobenzoic acid
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 3 h / 20 - 25 °C / Autoclave; Reflux 2.1: aluminum (III) chloride / dichloromethane / 5 h / 0 - 5 °C / Autoclave; Large scale 3.1: iron; ammonium chloride / ethanol; water / 5 h / 78 - 80 °C / Autoclave; Large scale 4.1: sodium nitrite; sulfuric acid / water / 0 - 10 °C / Large scale 4.2: 0.5 h / 0 - 20 °C / Large scale View Scheme |
2-chloro-5-nitrobenzoylchloride
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / dichloromethane / 5 h / 0 - 5 °C / Autoclave; Large scale 2.1: iron; ammonium chloride / ethanol; water / 5 h / 78 - 80 °C / Autoclave; Large scale 3.1: sodium nitrite; sulfuric acid / water / 0 - 10 °C / Large scale 3.2: 0.5 h / 0 - 20 °C / Large scale View Scheme |
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
(2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone
Conditions | Yield |
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With acetylhydroxamic acid; potassium carbonate In dimethyl sulfoxide at 80℃; for 6h; | 95.4% |
(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone
ethanol
(2-chloro-5-iodo-phenyl)-(4-ethoxyphenyl)methanone
Conditions | Yield |
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With sodium hydroxide at 50 - 65℃; Temperature; Reagent/catalyst; | 94.3% |
(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% |