(2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone

Base Information

• Chemical Name: (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone
• CAS No.: 915095-87-3
• Molecular Formula: C17H14ClIO3
• Molecular Weight: 428.654
• Mol file: 915095-87-3.mol

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

Chemical Property of (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone

Chemical Property:

• Boiling Point: 526℃
• Flash Point: 272℃
• PSA: 35.53000
• Density: 1.639
• LogP: 4.34330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

≥98.0% ^*data from raw suppliers

(2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone is an intermediate of Empagliflozin (E521510) which is a potent and selective SGLT-2 inhibitor that improves glycaemic control syndrome in diabetic rats.

Technology Process of (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone

There total 15 articles about (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.8%

(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone (915095-86-2) + (S)-3-hydroxytetyrahydrofurane (86087-23-2,84921-89-1,864447-89-2) → (S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-87-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 16 - 25 ℃; for 3h;

Reference yield: 87.0%

(2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone (1459754-40-5) + (R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate (219823-47-9) → (S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-87-3)

Guidance literature:

With potassium carbonate; potassium iodide; In acetonitrile; at 50 - 55 ℃;

Reference yield: 81.0%

2-chloro-5-iodobenzoic acid (19094-56-5) + (S)-3-phenoxytetrahydrofuran → (S)-(2-chloro-5-iodophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (915095-87-3)

Guidance literature:

2-chloro-5-iodobenzoic acid; With oxalyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 4h;

(S)-3-phenoxytetrahydrofuran; With aluminum (III) chloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1007/s00044-019-02299-4

upstream raw materials:

(2-chloro-5-iodophenyl)(4-fluorophenyl)methanone

(S)-3-hydroxytetyrahydrofurane

fluorobenzene

2-chloro-5-iodobenzoic acid

Downstream raw materials:

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

(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

C₃₁H₃₅ClO₁₁

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