1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: 1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane
• CAS No.: 1272667-61-4
• Molecular Formula: C₂₀H₂₉BO₄
• Molecular Weight: 344.259
• Mol file: 1272667-61-4.mol

Synonyms:1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane

Chemical Property of 1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane

There total 9 articles about 1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane 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: 53.0%

3-Bromophenol (591-20-8) + 1-methyl-4-methylenecyclohexanol (1272667-64-7) + bis(pinacol)diborane (73183-34-3) → 1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane (1272667-61-4)

Guidance literature:

1-methyl-4-methylenecyclohexanol; With Acetyl cyanide; iodine; sodium carbonate; at 25 ℃; for 1h;

3-Bromophenol; With Acetyl cyanide; potassium carbonate; at 150 ℃; for 48h; Sealed tube;

bis(pinacol)diborane; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃; for 15h;

DOI:10.1016/j.bmcl.2016.02.075

Reference yield:

1-(3-bromophenoxymethyl)-4-methyl-7-oxabicyclo[2.2.1]heptane (1272667-62-5) + bis(pinacol)diborane (73183-34-3) → 1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane (1272667-61-4)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 80 ℃; for 15h; Inert atmosphere;

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 1-methyl-4-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxymethyl]-7-oxabicyclo[2.2.1]heptane (1272667-61-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diethyl ether / 4.5 h / 20 °C

2.1: hydrogenchloride; water / 48 h / 20 °C

3.1: toluene-4-sulfonic acid / 1 h / 20 °C

4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -10 °C

4.2: 21 h / -10 - 20 °C

5.1: toluene-4-sulfonic acid / methanol / 24 h / 20 °C

6.1: iodine; sodium carbonate / acetonitrile / 1 h / 20 °C

7.1: potassium carbonate / acetonitrile / 20 - 150 °C / Inert atmosphere

8.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; water; iodine; potassium acetate; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

cyclohexanedione monoethylene ketal

1-(3-bromophenoxymethyl)-4-methyl-7-oxabicyclo[2.2.1]heptane

bis(pinacol)diborane

8-methyl-1,4-dioxa-spiro[4.5]decan-8-ol