methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

Base Information

Chemical Name:methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate
CAS No.:1565857-84-2
Molecular Formula:C₂₀H₂₃BO₄
Molecular Weight:338.211
Hs Code.:

Synonyms:methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

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Chemical Property of methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

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Technology Process of methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

There total 5 articles about methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate 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: 83.0%

: 619-42-1
4-methoxycarbonylphenyl bromide

: 1565857-71-7
trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)stannane

: 1565857-84-2
methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃; for 12h; chemoselective reaction; Inert atmosphere;
DOI:10.1021/jo402618r

Reference yield:

: 210907-84-9
3-aminophenylboronic acid pinacolate

: 1565857-84-2
methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 4 h / 0 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / 110 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; toluene; 2: |Stille Cross Coupling;
DOI:10.1021/jo402618r

Reference yield:

: 68716-48-3
4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane

: 1565857-84-2
methyl 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 5%-palladium/activated carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr

2: tert.-butylnitrite; toluene-4-sulfonic acid / 1,2-dichloro-ethane / 4 h / 0 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / 110 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; 5%-palladium/activated carbon; hydrogen; toluene-4-sulfonic acid; In methanol; 1,2-dichloro-ethane; toluene; 3: |Stille Cross Coupling;
DOI:10.1021/jo402618r