5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene

Base Information

• Chemical Name: 5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene
• CAS No.: 873895-66-0
• Molecular Formula: C₂₄H₂₈BrNS₂
• Molecular Weight: 474.529

Synonyms:5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene

Chemical Property of 5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene

Chemical Property:

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Technology Process of 5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene

There total 2 articles about 5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene 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: 82.0%

N,N-dibutylamino-4-(diethoxyphosphoryl)methylbenzene (131719-50-1) + 5'-bromo-2,2'-bithiophene-5-carboxaldehyde (110046-60-1) → 5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene (873895-66-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1039/b510826h

Reference yield:

diethyl (4-aminobenzyl)phosphonate (20074-79-7) → 5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene (873895-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / Heating

2: 82 percent / t-BuOK / tetrahydrofuran / 1 h / 25 °C

With potassium tert-butylate; potassium carbonate; In tetrahydrofuran; 2: Horner-Emmons-Wittog olefination;

DOI:10.1039/b510826h

Reference yield: 52.0%

5'-bromo-5-[(E)-4-(4-N,N-dibutylaminobenzylidene)methyl]-2,2'-bithiophene (873895-66-0) + 2,5-bis(tributylstannyl)thiophene (145483-63-2) → 5,5''''-bis[(E,E)-(4-N,N-dibutylaminobenzylidene)methyl]-2,2':5',2'':5'',2''':5''',2''''-quinquetiophene

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 100 ℃; for 18h;

DOI:10.1039/b510826h

upstream raw materials:

N,N-dibutylamino-4-(diethoxyphosphoryl)methylbenzene

5'-bromo-2,2'-bithiophene-5-carboxaldehyde

diethyl (4-aminobenzyl)phosphonate

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