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Author: Subject: Tosylate to Alkyl Azide reference please
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[*] posted on 12-4-2021 at 12:07
Tosylate to Alkyl Azide reference please


I planned on performing the fairly common substitution of tosylate to alkyl azide with sodium azide, but for some reason I can't find references for the exact procedure anywhere. Does anyone have a reference for the procedure or can at least point me in the right direction? Thank you.
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solo
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[*] posted on 12-4-2021 at 14:42


.....here is a lead....solo

https://www.organic-chemistry.org/synthesis/C1N/azides/alkyl...




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[*] posted on 12-4-2021 at 17:02


Yeah I saw that. There was only one for tosylates to alkl azide and it required a microwave. I've never done microwave chemistry and I'd rather not. Honestly I thought it was only going to take 30 seconds of searching and I thought all I was really searching for was molar ratios along with solvent type. I thought it was that simple a reaction since tosylate is such a good leaving group and azides are so reactive. I really thought it was a quick mix. But I actually can't find much of anything.
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AvBaeyer
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[*] posted on 12-4-2021 at 19:00


Many years ago I ran the reaction you are interested in. The reaction with sodium azide and a tosylate (or alkyl halide) was carried out in aqueous ethanol. The procedure in the following reference was used:

Brenner, M. and Reichenbacher, HR, Helv. Chem. Acta. 1958, v41, 181-188.

Isolated yields were in the range of 70%- 80%.

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[*] posted on 13-4-2021 at 10:30


^^^ Thank you very much.
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zed
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[*] posted on 18-4-2021 at 14:17


Yes. I have seen very few references to the use of Tosylates. Handy they can be. Seems you might be able to utilize Tosylates to Methylate Phenols. Very convenient, and perhaps less volatile and toxic, than some of the standard reagents.

I'll see if I can dig something up. Halides are more common.

Did see this out there. https://www.thieme-connect.de/products/ejournals/abstract/10...

https://en.wikipedia.org/wiki/Tosyl_azide

Ummm. I'm not making much progress, conditions would probable mess up your azide.

703
Phenetole: Phenol (19 g, 0.2 mole) is dissolved in 3N-sodium hydroxide solution (0.2 mole
of NaOH), treated with ethyl />-toluenesulfonate (40 g), and heated and stirred under reflux on a boiling water-bath. Further 6N-sodium hydroxide solution (10 ml) was added and the whole heated for a further 30 min. After cooling, the upper, organic, layer was taken up in
ether, washed with dilute sodium hydroxide solution, dried, and evaporated. The residue, 20 distilled in a vacuum, gave the ethyl ether (19.2 g, 78.7%), nD 1.5075.

Onward.

A decent reference... Page 477
Not exactly what you are looking for, but closer.

https://ipfs.io/ipfs/bafykbzacebdzqhndbsjnuqfph4o27raupmq6as...

OK. The fellers over at "Masters of Organic Chemistry"

Do have a little spiel on the subject, and perhaps a few references:

https://www.masterorganicchemistry.com/2018/06/29/some-react...

Me? I'll read up on it later. I'm running out of steam.
Sometimes, I have to sleep.

Brosylates? https://pubs.acs.org/doi/abs/10.1021/ja00377a057

Turns out Brosylates, are in the ball park.

[Edited on 19-4-2021 by zed]

[Edited on 19-4-2021 by zed]

[Edited on 19-4-2021 by zed]
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[*] posted on 18-4-2021 at 14:28


Crap I haven't answered your pm yet, I'll get to that, no worries.
Sorry for the delay though...
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