5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene

Base Information

• Chemical Name: 5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene
• CAS No.: 937281-16-8
• Molecular Formula: C₁₅H₁₇BO₂S
• Molecular Weight: 272.176
• Mol file: 937281-16-8.mol

Synonyms:5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene

Chemical Property of 5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene

There total 1 articles about 5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene 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: 40.0%

4-bromo-2-phenyl thiophene (38071-58-8) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene (937281-16-8)

Guidance literature:

4-bromo-2-phenyl thiophene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.583333h;

With Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 3.5h;

2,2-Dimethyl-1,3-propanediol; With acetic acid; In tetrahydrofuran; at 20 ℃; for 0.416667h;

DOI:10.1021/jm070038n

Reference yield: 51.0%

5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene (937281-16-8) + 3-benzyloxy-4-iodo-5-(1-methoxycarbonyl-4-piperidyl)isoxazol (841259-40-3) → 3-benzyloxy-4-[(5-phenyl)-3-thienyl]-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 22h;

DOI:10.1021/jm070038n

Reference yield:

5-phenyl-3-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)thiophene (937281-16-8) → 4-[(5-phenyl)-3-thienyl]-5-(4-piperidinyl)-3-isoxazolol hydrobromide

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / Pd(PPh₃)2Cl₂; aq. K₂CO₃ / dimethylformamide / 22 h / 70 °C

2: 58 percent / HBr; AcOH / 24 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; hydrogen bromide; potassium carbonate; acetic acid; In N,N-dimethyl-formamide; 1: Suzuki coupling;

DOI:10.1021/jm070038n

upstream raw materials:

4-bromo-2-phenyl thiophene

2,2-Dimethyl-1,3-propanediol