1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol

Base Information

• Chemical Name: 1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol
• CAS No.: 1467059-89-7
• Molecular Formula: C₁₅H₂₁BO₃
• Molecular Weight: 260.141
• Mol file: 1467059-89-7.mol

Synonyms:1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol

Chemical Property of 1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol

There total 2 articles about 1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-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: 95.0%

1-(4-bromophenyl)cyclobutan-1-ol (19936-14-2) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol (1467059-89-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110 ℃;

DOI:10.1021/acs.oprd.8b00059

Reference yield:

1.4-dibromobenzene (106-37-6) → 1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol (1467059-89-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -100 - -75 °C / Inert atmosphere; Large scale

1.2: 0.5 h / -75 - -15 °C / Inert atmosphere; Large scale

2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 110 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; potassium acetate; In tetrahydrofuran; 1,4-dioxane; hexane;

DOI:10.1021/acs.oprd.8b00059

Reference yield: 95.0%

1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)cyclobutan-1-ol (1467059-89-7) + 5-bromo-4,6-difluoro-1H-indole-3-carbaldehyde (1467059-98-8) → 4,6-difluoro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carbaldehyde (1467059-99-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In ethanol; water; toluene; at 115 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01641

upstream raw materials:

1-(4-bromophenyl)cyclobutan-1-ol

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

1.4-dibromobenzene

Downstream raw materials:

6-chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid

5-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carbaldehyde

5-[4-(1-hydroxycyclobutyl)phenyl]-6-methyl-1H-indole-3-carboxylic acid

3-formyl-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-6-carbonitrile