4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl

Base Information

Chemical Name:4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl
CAS No.:1338777-83-5
Molecular Formula:C₂₈H₄₀B₂O₈
Molecular Weight:526.243
Hs Code.:

Synonyms:4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl

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Chemical Property of 4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl

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Technology Process of 4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl

There total 4 articles about 4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl 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: 70.0%

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 200943-34-6
4-bromo-1-(4-bromo-2,5-dimethoxyphenyl)-2,5-dimethoxybenzene

: 1338777-83-5
4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl

Guidance literature:: With (CH₃)3CLi; In tetrahydrofuran; pentane; (CH3)3CLi in pentane added dropwise to a soln. of (C6H2(OCH3)2Br)2 in THF at -78°C, stirred for 1 h at -78°C, B compd. added dropwise, allowed to warm to room temp. and stirred overnight; THF-removed (vac.), H2O added, neutralised with HCl soln., extd. (CH2Cl2), the org. phase dried (Na2SO4), solvent-removed, recrystd. (petrol);
DOI:10.1039/c1dt10667h

Reference yield:

: 4555-64-0
2,2',5,5'-tetramethoxybiphenyl

: 1338777-83-5
4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-Bromosuccinimide / dichloromethane / 10 h / Reflux

2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C

2.2: -78 - 20 °C

With N-Bromosuccinimide; tert.-butyl lithium; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1039/c1dt10667h

Reference yield:

: 25245-34-5
1-bromo-2,5-dimethoxybenzene

: 1338777-83-5
4,4′-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan)-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl

Guidance literature:: Multi-step reaction with 3 steps

1.1: bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere

2.1: N-Bromosuccinimide / dichloromethane / 10 h / Reflux

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C

3.2: -78 - 20 °C

With N-Bromosuccinimide; bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; tert.-butyl lithium; zinc; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1039/c1dt10667h