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Topic: Propionyl Bromide using 48% HBr  (Read 7837 times)

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Offline yoyoils

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Propionyl Bromide using 48% HBr
« on: December 24, 2011, 09:38:16 PM »
Since it's possible to synthesize 2-bromopropane from Isopropyl alcohol using HBr 48%

I was wondering if you could make Propionyl Bromide the same way using Propionic acid + 48% HBr?

I'm just thinking if Br2, Br, or HBr won't effect acetone or MEK but it does attack the hydroxy group then im preying this can work....

Offline yoyoils

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Re: Propionyl Bromide using 48% HBr
« Reply #1 on: December 25, 2011, 01:52:59 AM »
Just found out it does effect acetone and MEK... so would it still be possible to make propionyl bromide with HBr or Br? I wish to halogenate propionic acid with either bromine or chlorine but I don't wanna deal with PCl3 even if I could make it and PBr3 is also impossible for me to make or use

Offline discodermolide

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Re: Propionyl Bromide using 48% HBr
« Reply #2 on: December 25, 2011, 05:09:22 AM »
Just found out it does effect acetone and MEK... so would it still be possible to make propionyl bromide with HBr or Br? I wish to halogenate propionic acid with either bromine or chlorine but I don't wanna deal with PCl3 even if I could make it and PBr3 is also impossible for me to make or use

If you keep the system anhydrous it may be possible. Usually one uses thionyl bromide (or thionyl chloride for the acyl chloride). This will give you the acyl bromide.

The use of PBr3 is the Hell-Vollhardt-Zelinsky reaction and puts the halogen on the carbon atom alpha to the carbonyl group.
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Offline yoyoils

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Re: Propionyl Bromide using 48% HBr
« Reply #3 on: December 29, 2011, 04:10:35 PM »
Yea I definitely don't want to use PBr3 then. Not interested in having it alpha to the carbonyl group. wants it on the other side :)


Would I be able to make Anhydrous Aluminium Trichloride if i setup small flask with aluminium-foil shavings and filled it with chlorine gas hooked to a reflux condenser with a balloon ontop and used a stove to heat it until it reacts? I'm not sure how hot it has to be and if that setup could explode at me badly

Offline discodermolide

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Re: Propionyl Bromide using 48% HBr
« Reply #4 on: December 29, 2011, 04:18:54 PM »
Yea I definitely don't want to use PBr3 then. Not interested in having it alpha to the carbonyl group. wants it on the other side :)


Would I be able to make Anhydrous Aluminium Trichloride if i setup small flask with aluminium-foil shavings and filled it with chlorine gas hooked to a reflux condenser with a balloon ontop and used a stove to heat it until it reacts? I'm not sure how hot it has to be and if that setup could explode at me badly
Do not use that set up.
Use thionyl chloride to make the acid chloride.
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Offline yoyoils

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Re: Propionyl Bromide using 48% HBr
« Reply #5 on: December 29, 2011, 05:52:36 PM »
Alright, I'll take your word for it! but still I don't know how to make or buy thionyl chloride though. Do you know any suppliers? or a method I could study? that's possible lol

Offline CaverKat

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Re: Propionyl Bromide using 48% HBr
« Reply #6 on: December 29, 2011, 08:17:23 PM »
http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=230464|SIAL&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC

Then you could also check Merck, Alfa, etc...

Offline discodermolide

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Re: Propionyl Bromide using 48% HBr
« Reply #7 on: December 29, 2011, 10:28:46 PM »
Alright, I'll take your word for it! but still I don't know how to make or buy thionyl chloride though. Do you know any suppliers? or a method I could study? that's possible lol

Look at Vogel's book on practical organic chemistry. It will tell you how to make the acid chloride and may even show you the apparatus. I have a copy here somewhere, but would need to scan it in, after I find it that is!
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Offline yoyoils

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Re: Propionyl Bromide using 48% HBr
« Reply #8 on: December 29, 2011, 11:47:09 PM »
http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=230464|SIAL&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC

Then you could also check Merck, Alfa, etc...


I didn't know I could make orders shipped to residential locations from them, and if so isn't that chemical a little bit of a red flag to them for notify officials. I wouldn't buy a lot but it's a freakin used in making nerge agent of sorts. How is that of help lol

Quote from: discodermolide
Look at Vogel's book on practical organic chemistry. It will tell you how to make the acid chloride and may even show you the apparatus. I have a copy here somewhere, but would need to scan it in, after I find it that is!

I will do! Thanks for that btw. Um except you mean it tells me how to it convert carboxylic acids to acyl chlorides? I rly need to know how to make SOCl2 or buy it from someplace that isn't going to red flag me. I'm looking for a small amount too

Offline discodermolide

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Re: Propionyl Bromide using 48% HBr
« Reply #9 on: December 30, 2011, 03:50:44 AM »
Why are you worried about getting flagged?
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Offline Arkcon

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Re: Propionyl Bromide using 48% HBr
« Reply #10 on: December 30, 2011, 11:21:08 AM »
OK, I'm going to lock this thread at this point.  And I'd like everyone who visits to examine this sort of thing carefully.  If someone wants to learn more about organic chemistry, I don't want to read about using a stove, I want to hear about them in a university laboratory using the steam bath.  When someone suggests just buying a reagent, which is typical for a university or production laboratory, I expect them to clear DEA permits with the appropriate office or their company's legal department, not shock, awe, and a 'lol'.

yoyoils:, try to stay more theoretical in your questions.  Try to gain practical laboratory information from textbooks and university courses, whether you've making an obscure organic compound, or an inorganic precursor that needs special handling, as in the case of this thread. http://www.chemicalforums.com/index.php?topic=54201.msg198106#msg198106
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

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