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Topic: synthesis of carbazole  (Read 1461 times)

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Offline GeorgiaMJ

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synthesis of carbazole
« 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?

Offline OrganicDan96

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Re: synthesis of carbazole
« Reply #1 on: March 24, 2019, 05:56:56 PM »
any other Pd complexes available?

Offline GeorgiaMJ

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Re: synthesis of carbazole
« Reply #2 on: March 25, 2019, 05:39:05 AM »
No :(

Offline MollyCooL

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Re: synthesis of carbazole
« Reply #3 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
Chinese Journal of Catalysis, 2010, 31 (11–12), 2010, pp 1439-1444
DOI: 10.1016/S1872-2067(10)60129-5
« Last Edit: April 03, 2019, 03:52:10 PM by Mitch »

Offline EngPet

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Re: synthesis of carbazole
« Reply #4 on: March 30, 2019, 10:00:25 AM »
Here are the reported conditions from the whole web, I hope it helps you

Offline kriggy

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Re: synthesis of carbazole
« Reply #5 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

Offline zarhym

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Re: synthesis of carbazole
« Reply #6 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.

 

Offline zarhym

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Re: synthesis of carbazole
« Reply #7 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.
« Last Edit: April 06, 2019, 02:26:30 AM by zarhym »

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