5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol

Base Information

• Chemical Name: 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol
• CAS No.: 1048361-41-6
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.275
• Mol file: 1048361-41-6.mol

Synonyms:

Chemical Property of 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol

There total 4 articles about 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol 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: 90.0%

5-methyl-2-(2-oxo-2-phenylethoxy)-phenyl boronic acid (923595-10-2) → 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol (1048361-41-6,923595-24-8)

Guidance literature:

With potassium phosphate; water; palladium diacetate; In 1,4-dioxane; at 100 ℃;

DOI:10.1016/j.tet.2008.05.056

Reference yield: 63.0%

(3-bromo-2-methoxy-5-methylphenyl)(phenyl)methanone (6723-10-0) → 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol (1048361-41-6,923595-24-8)

Guidance literature:

With palladium⁽⁰⁾bis(tricyclohexylphosphine); cesium pivalate; In toluene; at 160 ℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1002/anie.201908460

Reference yield:

phenylmagnesium bromide (100-58-3) → 5-methyl-3-phenyl-2,3-dihydrobenzofuran-3-ol (1048361-41-6,923595-24-8)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 1 h / -78 - 25 °C / Inert atmosphere

2: pyridinium chlorochromate; silica gel / dichloromethane

3: palladium⁽⁰⁾bis(tricyclohexylphosphine); cesium pivalate / toluene / 16 h / 160 °C / Inert atmosphere; Sealed tube; Glovebox

With palladium⁽⁰⁾bis(tricyclohexylphosphine); silica gel; cesium pivalate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/anie.201908460

upstream raw materials:

5-methyl-2-(2-oxo-2-phenylethoxy)-phenyl boronic acid

phenylmagnesium bromide

(3-bromo-2-methoxy-5-methylphenyl)(phenyl)methanone

Refernces

• 1、 Liu, Guixia,Lu, Xiyan. "Palladium(II)-catalyzed intramolecular addition of arylboronic acids to ketones". . p. 7324 - 7330. Retrieved 2008/12/20.