2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester

Base Information

• Chemical Name: 2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester
• CAS No.: 1351501-00-2
• Molecular Formula: C₁₇H₂₄BFO₄
• Molecular Weight: 322.185
• Hs Code.: 2931900090
• Mol file: 1351501-00-2.mol

Synonyms:

Chemical Property of 2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

(4-(Tert-Butoxycarbonyl)-3-Fluorophenyl)BoronicAcidPinacolEster ^*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)-benzoic acid tert-butyl ester

There total 2 articles about 2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl 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: 90.0%

4-bromo-2-fluoro-benzoic acid tert-butyl ester (889858-12-2) + bis(pinacol)diborane (73183-34-3) → tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1351501-00-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 95 ℃; for 16h; Solvent; Temperature; Concentration; Inert atmosphere;

Reference yield:

2-fluoro-4-bromobenzoic acid (112704-79-7) → tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1351501-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide; oxalyl dichloride / tetrahydrofuran / 1.5 h / 0 - 20 °C

1.2: 64 h / 20 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 16 h / 95 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; oxalyl dichloride; potassium acetate; N,N-dimethyl-formamide; In tetrahydrofuran; 1,4-dioxane;

Reference yield:

tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1351501-00-2) → (S)-1-tert-butyl 2-methyl 4-(6-amino-5-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyridin-3-yl)-1H-pyrrole-1,2(2H,5H)-dicarboxylate

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; butan-1-ol / 100 °C / Inert atmosphere

2: N-Bromosuccinimide / acetonitrile / 0.17 h

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,2-dimethoxyethane / 110 °C / Inert atmosphere; Microwave irradiation

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate / tetrahydrofuran; water / 0.17 h / 90 °C / Inert atmosphere; Microwave irradiation

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; caesium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; acetonitrile; butan-1-ol; 1: |Suzuki Coupling;

upstream raw materials:

2-fluoro-4-bromobenzoic acid

4-bromo-2-fluoro-benzoic acid tert-butyl ester

bis(pinacol)diborane

Refernces