4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene

Base Information

Chemical Name:4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene
CAS No.:865479-40-9
Molecular Formula:C₁₈H₁₇BF₂N₂O
Molecular Weight:326.154
Hs Code.:

Synonyms:4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene

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Chemical Property of 4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene

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Technology Process of 4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene

There total 3 articles about 4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene 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: 82.0%

: 865479-49-8
5-(p-methoxyphenyl)-1,9-dimethyldipyrromethene

: 109-63-7
trifluoroborane diethyl ether

: 7087-68-5
N-ethyl-N,N-diisopropylamine

: 865479-40-9
4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene

Guidance literature:: In dichloromethane; dipyrromethene (0.5 mol) dissolved in CH2Cl2, DIEA (16 mmol) added, stirred at room temp. for 20 min (Ar), BF3*OEt2 (20 mmol) added dropwise, stirred for 1 h; mixt. washed (H2O, 2 N NaOH), aq. soln. extd. (CH2Cl2), dried over MgSO4, filtered, evapd., chromy. on silica gel (ethyl acetate/hexane 3/7 v/v), recrystd. (hexane/CHCl3);
DOI:10.1021/jp052626n

Reference yield: 21.0%

: 636-41-9
2-methyl-1H-pyrrole

: 109-63-7
boron trifluoride diethyl etherate

: 100-07-2
4-methoxy-benzoyl chloride

: 865479-40-9
4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene

Guidance literature:: 2-methyl-1H-pyrrole; 4-methoxy-benzoyl chloride; In 1,2-dichloro-ethane; at 120 ℃; for 16h; Inert atmosphere;

With triethylamine; In 1,2-dichloro-ethane; at 0 ℃; for 0.333333h; Inert atmosphere;

boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 20 ℃; for 20h; Inert atmosphere;
DOI:10.1016/j.ica.2018.06.006

Reference yield:

: 1003-29-8,254729-95-8
2-pyrrole aldehyde

: 865479-40-9
4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hydroxide; hydrazine hydrate / ethylene glycol / 3.5 h / 80 - 180 °C / Inert atmosphere

2.1: 1,2-dichloro-ethane / 16 h / 120 °C / Inert atmosphere

2.2: 0.33 h / 0 °C / Inert atmosphere

2.3: 20 h / 20 °C / Inert atmosphere

With hydrazine hydrate; potassium hydroxide; In ethylene glycol; 1,2-dichloro-ethane;
DOI:10.1016/j.ica.2018.06.006