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Topic: 2-(Chloromethyl)pyridine - recipe  (Read 2525 times)

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Offline Nekromantis

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2-(Chloromethyl)pyridine - recipe
« on: October 04, 2013, 09:45:32 AM »
Hi,

I need a recipe how to make a 2-(Chloromethyl)pyridine or 2-(bromomethyl)pyridine. I searched in internet but I don't found nothing special.  Someone help me?
Ph.D student of organic chemistry from Poland
Speciality: Ionic Liquids, Chiral Ionic Liquids, Diels-Alder reaction

Offline discodermolide

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Re: 2-(Chloromethyl)pyridine - recipe
« Reply #1 on: October 04, 2013, 09:50:17 AM »
You are a student of organic chemistry, according to the statement at the bottom of your posts. Have you no access to a university library?
Have you any ideas how one might make this (these compounds)?
Development Chemists do it on Scale, Research Chemists just do it!
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Offline Nekromantis

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Re: 2-(Chloromethyl)pyridine - recipe
« Reply #2 on: October 04, 2013, 09:57:26 AM »
I went back to my family home for the weekend and now i don't have a access to mu university datbase. I Found one website:

http://www.patentgenius.com/patent/4221913.html

but my promoter of my master science thesis want a article.
Ph.D student of organic chemistry from Poland
Speciality: Ionic Liquids, Chiral Ionic Liquids, Diels-Alder reaction

Offline kriggy

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Re: 2-(Chloromethyl)pyridine - recipe
« Reply #3 on: October 06, 2013, 04:07:37 AM »
You dont have distant acces to your library? You should ask about it, its very handy :)
Anyway, I´ve done this few weeks ago so I think I can help you:
using procedure from Bioorganic and Medicinal Chemistry,  2009 ,  vol. 17,  # 10   p. 3604 - 3617

5g of PyCHOH was dissolved in CHCl3 and cooled to 0°C. 27g of SOCl2 was added slowly so the temperature didnt rise over 10°C and the colour changed to  yellow-gree. After addition of all SOCl2 the mixture was stirred at RT for about 45 minutes. After 45 mins the mixture was basified to pH~8 by Na2CO3. After that the solution was extracted by 3x50ml of CHCl3. Organic layer was washed with 3x50 ml of water and dried over Na2SO4. After evaporation of solvent the red solution appeared and red crystals started to crystalize.

note: I have some impurities in my product due to impurities in starting material which i wasnt aware of when I started the reaction. So it is possible that your product will have different colour

Offline Nekromantis

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Re: 2-(Chloromethyl)pyridine - recipe
« Reply #4 on: October 06, 2013, 07:59:34 AM »
kriggy thank you very much! :)
Ph.D student of organic chemistry from Poland
Speciality: Ionic Liquids, Chiral Ionic Liquids, Diels-Alder reaction

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