(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Base Information

• Chemical Name: (2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
• CAS No.: 1082066-29-2
• Molecular Formula: C13H18BFO3
• Molecular Weight: 252.094
• Hs Code.: 2934999090
• Mol file: 1082066-29-2.mol

Synonyms:(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Chemical Property of (2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

Chemical Property:

• PSA: 38.69000
• LogP: 1.61720
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

3-Fluoro-4-(hydroxymethyl)phenylboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

There total 4 articles about (2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol 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: 76.0%

bis(pinacol)diborane (73183-34-3) + 4-bromo-2-fluorobenzyl alcohol (188582-62-9) → (2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (1082066-29-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 16h;

DOI:10.1016/j.ejmech.2019.06.049

Reference yield:

tetrapropylammonium 2-fluorobenzylsulfate + bis(pinacol)diborane (73183-34-3) → (2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (1082066-29-2) + [2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanol (1352733-99-3) + C19H29B2FO5

Guidance literature:

tetrapropylammonium 2-fluorobenzylsulfate; bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin; In 1,4-dioxane; at 40 ℃; for 12h; Glovebox;

With hydrogenchloride; In 1,4-dioxane; water; for 1h; Overall yield = 69 percent; Overall yield = 91.2 mg; regioselective reaction; Glovebox;

DOI:10.1021/jacs.9b08464

Reference yield:

2-fluorobenzyl alcohol (446-51-5) → (2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (1082066-29-2) + [2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanol (1352733-99-3) + C19H29B2FO5

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; sulfur trioxide pyridine complex / dichloromethane / 19 h / 20 - 40 °C

1.2: 1 h

2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin / 1,4-dioxane / 12 h / 40 °C / Glovebox

2.2: 1 h / Glovebox

With pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin; sulfur trioxide pyridine complex; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jacs.9b08464

upstream raw materials:

bis(pinacol)diborane

4-bromo-2-fluorobenzyl alcohol

2-fluorobenzyl alcohol

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