N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2

Base Information

• Chemical Name: N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2
• CAS No.: 945867-06-1
• Molecular Formula: C₃₁H₄₀BrNO₂Si
• Molecular Weight: 566.654
• Mol file: 945867-06-1.mol

Synonyms:N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2

Chemical Property of N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2

There total 4 articles about N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2 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: 56.0%

N-(3,5-dibromobenzyl)coumarin 2 (945867-05-0) + tris-iso-propylsilyl acetylene (89343-06-6) → N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2 (945867-06-1)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In triethylamine; at 80 ℃; for 48h;

DOI:10.1002/ejoc.200700118

Reference yield:

3,5-dibromobenzyl bromide (56908-88-4) → N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2 (945867-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / K₂CO₃ / acetonitrile / 120 h / Heating

2: 56 percent / Pd(PPh₃)4 / triethylamine / 48 h / 80 °C

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In triethylamine; acetonitrile; 2: Sonogashira coupling reaction;

DOI:10.1002/ejoc.200700118

Reference yield:

(3,5-dibromophenyl)methanol (145691-59-4) → N-{3-bromo-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2 (945867-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / carbon tetrabromide; triphenylphosphane / tetrahydrofuran / 16 h / 20 °C

2: 62 percent / K₂CO₃ / acetonitrile / 120 h / Heating

3: 56 percent / Pd(PPh₃)4 / triethylamine / 48 h / 80 °C

With carbon tetrabromide; potassium carbonate; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; triethylamine; acetonitrile; 3: Sonogashira coupling reaction;

DOI:10.1002/ejoc.200700118

upstream raw materials:

N-(3,5-dibromobenzyl)coumarin 2

tris-iso-propylsilyl acetylene

3,5-dibromobenzyl bromide

(3,5-dibromophenyl)methanol

Downstream raw materials:

N-{3-[2-(triisopropylsilyl)ethynyl]-5-[2-(trimethylsilyl)ethynyl]benzyl}coumarin 2

N-{3-ethynyl-5-[2-(triisopropylsilyl)ethynyl]benzyl}coumarin 2