(1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Base Information

• Chemical Name: (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester
• CAS No.: 1265356-47-5
• Molecular Formula: C₁₈H₁₉BO₅
• Molecular Weight: 326.157
• Mol file: 1265356-47-5.mol

Synonyms:(1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Chemical Property of (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

There total 9 articles about (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester 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: 46.0%

2-methyl-4-phenoxy-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (1265360-90-4) + ethyl bromoacetate (105-36-2) → (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (1265356-47-5)

Guidance literature:

ethyl bromoacetate; With chloro-trimethyl-silane; zinc; at 37 ℃; for 0.0833333h; Reflux;

2-methyl-4-phenoxy-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde; In tetrahydrofuran; at 0 ℃; for 4h;

With ammonium chloride; In tetrahydrofuran; water;

Reference yield:

phenylboronic acid (98-80-6) → (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (1265356-47-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper diacetate / pyridine; dichloromethane; acetonitrile / 20 °C / 4 ? Molecular sieve

2.1: boron tribromide / dichloromethane / 4 h / -78 - 20 °C / Cooling with acetone-dry ice

3.1: triethylamine / dichloromethane / 1 h / -78 °C

4.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

5.1: chloro-trimethyl-silane; zinc / 0.08 h / 37 °C / Reflux

5.2: 4 h / 0 °C

With chloro-trimethyl-silane; potassium acetate; boron tribromide; triethylamine; zinc; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper diacetate; In 1,4-dioxane; pyridine; dichloromethane; acetonitrile;

Reference yield:

2,4-dihydroxy-6-methylbenzaldehyde (487-69-4) → (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (1265356-47-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 18 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / Cooling with ice

2.2: 1 h / 20 °C

3.1: methanol / Amberlyst_.(R). 15 / 1 h / 50 °C

4.1: copper diacetate / pyridine; dichloromethane; acetonitrile / 20 °C / 4 ? Molecular sieve

5.1: boron tribromide / dichloromethane / 4 h / -78 - 20 °C / Cooling with acetone-dry ice

6.1: triethylamine / dichloromethane / 1 h / -78 °C

7.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

8.1: chloro-trimethyl-silane; zinc / 0.08 h / 37 °C / Reflux

8.2: 4 h / 0 °C

With methanol; chloro-trimethyl-silane; potassium acetate; boron tribromide; sodium hydride; triethylamine; zinc; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper diacetate; pyridinium p-toluenesulfonate; In 1,4-dioxane; pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;

upstream raw materials:

phenylboronic acid

2-methyl-4-phenoxy-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde

ethyl bromoacetate

2,4-dihydroxy-6-methylbenzaldehyde