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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: GeorgiaMJ on March 24, 2019, 04:45:00 PM

Title: synthesis of carbazole
Post by: GeorgiaMJ on March 24, 2019, 04:45:00 PM

So, for organic lab I have to synthesise 9-hexyl-3-bromo-6-nitrocarbazole. In one of my steps , actually my first I need to synthesise carbazole from diphenylamine . The problem is that in the lab Pd(OAc)2 is not available. I searched all the web for an other way to make this step but still I cant find something that doesnt involve Pd(OAC)2. I'm not still so sure about the mechanism of the reaction. So can I use something else instead?

Title: Re: synthesis of carbazole
Post by: OrganicDan96 on March 24, 2019, 05:56:56 PM

any other Pd complexes available?

Title: Re: synthesis of carbazole
Post by: GeorgiaMJ on March 25, 2019, 05:39:05 AM

No :(

Title: Re: synthesis of carbazole
Post by: MollyCooL on March 29, 2019, 10:43:57 PM

It’s highly unlikely but if you have the catalyst, the following paper might help.

Dehydrocyclization of Diphenylamine to Carbazole over Platinum-Based Bimetallic Catalysts (https://www.sciencedirect.com/science/article/pii/S1872206710601295)
Chinese Journal of Catalysis, 2010, 31 (11–12), 2010, pp 1439-1444
DOI: 10.1016/S1872-2067(10)60129-5 (https://doi.org/10.1016/S1872-2067(10)60129-5)

Title: Re: synthesis of carbazole
Post by: EngPet on March 30, 2019, 10:00:25 AM

Here are the reported conditions from the whole web, I hope it helps you

Title: Re: synthesis of carbazole
Post by: kriggy on April 01, 2019, 07:37:56 AM

@MollyCooL: I dont think this conditions are usefull.. Having the catalyst is one thing and  also heating to 400-500°C as they describe is something not commonly done in chemical labs

GeorgiaMJ: why dont you buy the catalyst? Its not as expensive (Fluorochem has 1g for £ 60,00

Title: Re: synthesis of carbazole
Post by: zarhym on April 06, 2019, 12:13:00 AM

You may try this photo irradiation approach.
This is a reaction I have done for many times.


For my reaction, 1g of diphenylsulfide requires about 20mg I₂, 500mL DCM and a quartz flask.
The reaction is completed after 40W UVC bulbs irradiation for 3 hours.

Methyloxirane is an oxidizer to regenerate of I₂, but I find out that it is not very important if I let the reaction done under air.

 

Title: Re: synthesis of carbazole
Post by: zarhym on April 06, 2019, 02:15:59 AM

FYI

The procedure in the attachment is from the supporting info of this paper: [10.1039/c5pp00466g].
By the way, I am the first author and the experiment was done when I was a graduate student.