2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

Base Information

Chemical Name:2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone
CAS No.:1360607-16-4
Molecular Formula:C₁₅H₂₂BFN₂O₂
Molecular Weight:292.161
Hs Code.:

Synonyms:2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

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Chemical Property of 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

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Technology Process of 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

There total 3 articles about 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone 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: 72.0%

: 455300-83-1
o-fluorobenzaldehyde N,N-dimethylhydrazone

: 73183-34-3
bis(pinacol)diborane

: 1360607-16-4
2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

Guidance literature:: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N,N-dibenzyl-N'-(pyridin-2-ylmethylene)hydrazine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 80 ℃; for 24h; regioselective reaction; Inert atmosphere;
DOI:10.1002/anie.201104544

Reference yield: 72.0%

: 455300-83-1
o-fluorobenzaldehyde N,N-dimethylhydrazone

: 73183-34-3
bis(pinacol)diborane

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 1360607-16-4
2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

Guidance literature:: With cat. [Ir(μ-OCH3)(C8H12)]2/2-C5H4NCHNN(CH2C6H5)2; In tetrahydrofuran; Sonication; dried Schlenk tube charged with dimethylhydrazone and diboron compd., added catalyst stock soln. (prepd. by sonication for 1 h) and pinacolborane, stirred at 80°C for 24 h; cooled to room temp., concd. to dryness, purified by column chromy. on neutral alumina (n-hexane/CH3COOC2H5);
DOI:10.1002/anie.201104544

Reference yield:

: 446-52-6
2-Fluorobenzaldehyde

: 1360607-16-4
2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

Guidance literature:: Multi-step reaction with 2 steps

1: magnesium sulfate / dichloromethane / 20 °C / Inert atmosphere

2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N,N-dibenzyl-N'-(pyridin-2-ylmethylene)hydrazine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N,N-dibenzyl-N'-(pyridin-2-ylmethylene)hydrazine; magnesium sulfate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; dichloromethane;
DOI:10.1002/anie.201104544