(E,E)-1-fluoro-2,5-bis-(3-hydroxy[⁽¹³⁾C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene

Base Information

• Chemical Name: (E,E)-1-fluoro-2,5-bis-(3-hydroxy[⁽¹³⁾C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene
• CAS No.: 1379597-78-0
• Molecular Formula: C₂₄H₁₇FO₆
• Molecular Weight: 426.34

Synonyms:(E,E)-1-fluoro-2,5-bis-(3-hydroxy[⁽¹³⁾C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene

Chemical Property of (E,E)-1-fluoro-2,5-bis-(3-hydroxy[⁽¹³⁾C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene

Chemical Property:

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Technology Process of (E,E)-1-fluoro-2,5-bis-(3-hydroxy[⁽¹³⁾C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene

There total 7 articles about (E,E)-1-fluoro-2,5-bis-(3-hydroxy[⁽¹³⁾C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene 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: 100.0%

(E,E)-1-fluoro-2,5-bis(3-methoxy[(13)C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene (1379597-76-8) → (E,E)-1-fluoro-2,5-bis-(3-hydroxy[(13)C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene (1379597-78-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 5h; Reflux;

DOI:10.1021/jo300746x

Reference yield:

(E,E)-1-fluoro-2,5-bis(3-methoxy[(13)C]carbonyl-4-methoxy-1,1',2,2'-tetradeuterostyryl)benzene (1379597-74-6) → (E,E)-1-fluoro-2,5-bis-(3-hydroxy[(13)C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene (1379597-78-0)

Guidance literature:

Multi-step reaction with 3 steps

1: boron tribromide / hexane; dichloromethane / -78 - 20 °C / Inert atmosphere

2: water / hexane; dichloromethane / 0 °C

3: potassium hydroxide / ethanol / 5 h / Reflux

With water; boron tribromide; potassium hydroxide; In ethanol; hexane; dichloromethane;

DOI:10.1021/jo300746x

Reference yield:

2-chloro-4-iodo-1-methoxybenzene (75676-72-1) → (E,E)-1-fluoro-2,5-bis-(3-hydroxy[(13)C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene (1379597-78-0)

Guidance literature:

Multi-step reaction with 6 steps

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 21 h / 45 °C / Inert atmosphere

2: bis(η3-allyl-μ-chloropalladium(II)); 1,1,1,2,2,2-hexamethyldisilane; water-d2; triphenylphosphine / N,N-dimethyl acetamide / 15 h / 80 °C / Inert atmosphere

3: 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; palladium diacetate; potassium carbonate / dimethyl sulfoxide / 20 h / 120 °C / Molecular sieve

4: boron tribromide / hexane; dichloromethane / -78 - 20 °C / Inert atmosphere

5: water / hexane; dichloromethane / 0 °C

6: potassium hydroxide / ethanol / 5 h / Reflux

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; 1,1,1,2,2,2-hexamethyldisilane; water; water-d2; palladium diacetate; boron tribromide; potassium carbonate; triethylamine; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide; 2: Shirakawa-Hayashi reduction;

DOI:10.1021/jo300746x

upstream raw materials:

4,4'-((2-fluoro-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-chloro-1-methoxybenzene)

(E,E)-1-fluoro-2,5-bis(3-chloro-4-methoxy-1,1',2,2'-tetradeuterostyryl)benzene

(E,E)-1-fluoro-2,5-bis(3-methoxy[⁽¹³⁾C]carbonyl-4-methoxy-1,1',2,2'-tetradeuterostyryl)benzene

(E,E)-1-fluoro-2,5-bis(3-methoxy[⁽¹³⁾C]carbonyl-4-hydroxy-1,1',2,2'-tetradeuterostyryl)benzene

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