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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: CasualGabe on September 15, 2021, 04:14:33 AM

Title: Esterification with bromine products
Post by: CasualGabe on September 15, 2021, 04:14:33 AM
Hi everyone,

I’m studying opiates and opioids for a full comprehension of the mu receptor.

I’m studying chemistry but much more bio chemistry so i need your help for a exercise.
I’m actually working on the capacity of the mu and kappa receptors in the brain (on mice, of course) and the key information is that an opiate with a long ester on the N or the 14 position penetrate deeper and better in the mu receptor, binding it very well like fentanyl does.

Picture 14-OH-opiate compound and you want to make a 14-esterification with phenylethyl bromide.

In which conditions will it be the best ? I know that bromine products are much more reactives than chlorines ones so i choose phenyethyl bromide as the key reagent.

Opiates are fragiles so i don’t want to heat it up or not too hot.

I was thinking of addind sulfuric acid as a catalyser and setting up a reflux and add the phenethyl bromide drop by drop.

What do you think about it ?


Kind regards,
Gabe.
Title: Re: Esterification with bromine products
Post by: rolnor on September 15, 2021, 05:18:53 AM
This is a ether formation, not esterification.
You can try cesium carbonate and phenethyl bromide in dimethyl sulphoxide. I dont  think you need heat. sonication in a ultrasonic bath can speed things up.
The fact that you suggest acid as catalyst shows that you need to do some reading, here is a start:
https://en.m.wikipedia.org/wiki/Williamson_ether_synthesis
Title: Re: Esterification with bromine products
Post by: Borek on September 15, 2021, 07:08:05 AM
Beware: this is close to drug synthesis which we don't discuss here.

I am leaving the thread open for now, but don't be surprised if it gets locked at some point.
Title: Re: Esterification with bromine products
Post by: CasualGabe on September 15, 2021, 07:42:05 AM
This is a ether formation, not esterification.
You can try cesium carbonate and phenethyl bromide in dimethyl sulphoxide. I dont  think you need heat. sonication in a ultrasonic bath can speed things up.
The fact that you suggest acid as catalyst shows that you need to do some reading, here is a start:
https://en.m.wikipedia.org/wiki/Williamson_ether_synthesis

Thank you. This is wonderful.

I don’t need any other information and I don’t want this subject to be inappropriate.

Kind regards everyone.
Title: Re: Esterification with bromine products
Post by: rolnor on September 15, 2021, 11:02:44 AM
Good!