2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1196396-03-8
• Molecular Formula: C₁₈H₁₉BF₂O₃
• Molecular Weight: 332.155
• Mol file: 1196396-03-8.mol

Synonyms:2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

Pinacol[4-(2,6-difluorophenoxy)phenyl]boronate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 6 articles about 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 75.0%

1,3-difluoro-2-(4-iodophenoxy)benzene (1414356-26-5) + bis(pinacol)diborane (73183-34-3) → 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1196396-03-8)

Guidance literature:

With potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 85 ℃; for 12h; Inert atmosphere;

Reference yield:

2-(4-bromophenoxy)-1,3-difluorobenzene + bis(pinacol)diborane (73183-34-3) → 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1196396-03-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 16h; Inert atmosphere;

Reference yield:

4-Fluoronitrobenzene (350-46-9,178603-76-4) → 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1196396-03-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.33 h / 0 - 20 °C

1.2: 12 h / 25 - 100 °C

2.1: hydrazine hydrate / methanol / 12 h / 25 °C / Inert atmosphere

3.1: hydrogenchloride; sodium nitrite / water / 0.58 h / 0 °C

3.2: 2 h / 25 °C

4.1: potassium acetate / palladium diacetate / N,N-dimethyl-formamide / 12 h / 85 °C / Inert atmosphere

With hydrogenchloride; potassium acetate; sodium hydride; hydrazine hydrate; sodium nitrite; palladium diacetate; In methanol; water; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

4-Fluoronitrobenzene

2,6-difluorophenol

1,3-difluoro-2-(4-iodophenoxy)benzene

bis(pinacol)diborane

Downstream raw materials:

tert-butyl (3R)-3-[4-amino-3-[4-(2,6-difluorophenoxy)-phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

3-[4-(2,6-difluorophenoxy)phenyl]-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

tert-butyl (2R)-2-([4-amino-3-[4-(2,6-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidine-1-carboxylate

3-[(3R)-3-[4-amino-3-[4-(2,6-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile

Refernces

• 1、 -. "Crystallization form of BTK inhibitor, and preparation method thereof". . . Retrieved 2017/08/31.
• 2、 -. "TREATMENT OF DRY EYE". . . Retrieved 2014/02/16.