(E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate

Base Information

• Chemical Name: (E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate
• CAS No.: 1622092-80-1
• Molecular Formula: C₁₇H₁₅BrO₄S
• Molecular Weight: 395.274
• Mol file: 1622092-80-1.mol

Synonyms:(E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate

Chemical Property of (E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate

There total 6 articles about (E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate 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: 85.0%

2-(2-ethynyl-4-methylphenoxy)ethyl 4-bromobenzenesulfonate (1622092-52-7) → (E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate (1622092-80-1)

Guidance literature:

With {1-cyclopentadecyl-3-[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(prop-1-yn-1-yl)gold; In benzene; at 90 ℃; for 15h; Sealed tube;

DOI:10.1002/anie.201310280

Reference yield:

4-bromobenzenesulfonyl chloride (98-58-8) → (E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate (1622092-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; pyridine / dichloromethane / 5 h / 0 - 20 °C

2: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 19 h / 0 - 20 °C

3: {1-cyclopentadecyl-3-[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(prop-1-yn-1-yl)gold / benzene / 15 h / 90 °C / Sealed tube

With pyridine; dmap; {1-cyclopentadecyl-3-[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(prop-1-yn-1-yl)gold; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1002/anie.201310280

Reference yield:

2-bromo-p-cresol (6627-55-0) → (E)-(6-methyl-2,3-dihydro-4H-chromen-4-ylidene)methyl 4-bromobenzenesulfonate (1622092-80-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1H-imidazole / dichloromethane / 1 h / 20 °C

2: triethylamine; copper(l) iodide; XPhos; palladium diacetate / 64 h / 50 °C / Inert atmosphere

3: tetra-n-butylammoniumfluoride trihydrate / tetrahydrofuran / 0.25 h / 20 °C

4: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 19 h / 0 - 20 °C

5: {1-cyclopentadecyl-3-[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(prop-1-yn-1-yl)gold / benzene / 15 h / 90 °C / Sealed tube

With 1H-imidazole; copper(l) iodide; {1-cyclopentadecyl-3-[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(prop-1-yn-1-yl)gold; palladium diacetate; tetra-n-butylammoniumfluoride trihydrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; XPhos; In tetrahydrofuran; dichloromethane; benzene; 2: |Sonogashira Cross-Coupling;

DOI:10.1002/anie.201310280

upstream raw materials:

4-bromobenzenesulfonyl chloride

2-bromo-p-cresol

2-hydroxyethyl 4-bromobenzenesulfonate

2-ethynyl-4-methylphenol

Refernces