September 21, 2024, 04:07:23 PM
Forum Rules: Read This Before Posting


Topic: Adding a keto group to bromo benzene in the place of the bromine?  (Read 3655 times)

0 Members and 1 Guest are viewing this topic.

Offline olly2323

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
So I want to add a keto group (-COCH2CH2CH3) to bromo benzene in the place of the bromine. Do i need to make an organometallic and then an acyl chloride?

Thanks for your help.

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5673
  • Mole Snacks: +328/-24
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #1 on: March 09, 2016, 11:49:43 AM »
Which organometallic reagent would you use?

Offline olly2323

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #2 on: March 09, 2016, 11:53:44 AM »
Which organometallic reagent would you use?

I was thinking possibly adding magnesium?

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5673
  • Mole Snacks: +328/-24
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #3 on: March 09, 2016, 01:16:12 PM »
A Grignard reagent may not work in this instance, because you might get addition to the ketone.  I would look at other organometallic reagents.  BTW do you have to start with the bromine-derivative, or could you use something else?

Offline olly2323

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #4 on: March 09, 2016, 01:18:36 PM »
Could start with something else.
« Last Edit: March 09, 2016, 03:00:16 PM by Arkcon »

Offline olly2323

  • New Member
  • **
  • Posts: 4
  • Mole Snacks: +0/-0
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #5 on: March 09, 2016, 02:36:29 PM »
What would you suggest, I dont really know?
« Last Edit: March 09, 2016, 03:00:34 PM by Arkcon »

Offline Arkcon

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7367
  • Mole Snacks: +533/-147
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #6 on: March 09, 2016, 03:06:25 PM »
I'd like to welcome you, olly2323:, to the Chemical Forums, but I'm going to ask you to read the Forum Rules{click}

This is a learning forum, we like to help people help themselves.  You'll have to arrive with some of the basics, and be able to respond to a hint.  Can you start with something you've learned recently?  You wanted to "add magnesium" , but Babcock_Hall: suggests a Grignard reagent wouldn't work.  Do you know what a Grignard reagent is, and how it works?  Can you find out in your textbook or class notes?  Its not likely you've been assigned a moderately advanced organic synthesis, without having had some prior instruction.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline Arkcon

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7367
  • Mole Snacks: +533/-147
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #7 on: March 09, 2016, 03:12:20 PM »
Oh, by the way, a common name for your assigned reagent is Butyrophenone, and its a common starting point for many medicines.  https://en.wikipedia.org/wiki/Butyrophenone  I hope you'll pay attention to the forum rules, and remember to keep this discussion firmly in the "school assignment" mode.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline critzz

  • Full Member
  • ****
  • Posts: 99
  • Mole Snacks: +7/-0
  • Gender: Male
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #8 on: March 09, 2016, 07:22:57 PM »
The grignard reaction might work if you use the weinreb amide of your keto group instead of an acyl chloride.

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

Offline zarhym

  • Full Member
  • ****
  • Posts: 118
  • Mole Snacks: +14/-1
  • Gender: Male
    • Linkedin
Re: Adding a keto group to bromo benzene in the place of the bromine?
« Reply #9 on: March 09, 2016, 07:39:29 PM »
Oh, by the way, a common name for your assigned reagent is Butyrophenone, and its a common starting point for many medicines.  https://en.wikipedia.org/wiki/Butyrophenone  I hope you'll pay attention to the forum rules, and remember to keep this discussion firmly in the "school assignment" mode.

Your target molecule is indeed commercially available and inexpensive.
However, if you still have to do this for some reason, I will suggest this method.
http://www.organic-chemistry.org/abstracts/lit2/214.shtm

Sponsored Links