Give chilled diluted sodium bicarbonate wash to your chlorinated compound taken in a organic solvent like DCM.Then distilled your compound under vacumme in buchhi .

Dear Sir,

I already tried very dilute sodium carbonate. Also, I have tried using just water, and I found that compound degraded to its corresponding alcohol in less than a minute.

So, which ever base I use, water will ultimately degrade the compound.

Is there any other way to clean the compound?

Thanks

Sachin

I made prenyl bromide to prenyl alcohol and i needed really pure version of the bromide. First make sure that the work up is the only problem. If possible use hydrocarbon instead of ether as an extracting solvent. I used to keep all my glasswares in the fridge. All water/carbonate wash solution were ice cold. I was super quick while working up.

If possible let us know what class of compound you are trying to purify.

Have you considered using phase transfer catalysis?

https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-1974-23231

Have you tried freeze drying (lyophylization)?  This sublimes out water and other volatiles from the frozen product. We use it on our pseudopeptides isolated from prep HPLC with volatile buffer components (HCl would qualify as volatile in some cases, it depends on whether it is bound to a strong base or not). 

My final text was not used, or maybe it will show up later. I started off by saying "Good comments above." I then changed volatile buffers components to volatile mobile phase components (such as formic acid). This should make more sense than the text that I see above. Best wishes. 

I think chlorination is not complete added two drops of DMF in your reaction during chlorination.

Hello sir,

To remove the acid, you can prepare 10% bicarbonate of soduim in water, then put the product in a quantity of dichloromethane and add the solution to prepare and to weigh it in agitation 5 hours, then decantation, to dry and concentrate your product

have a nice week end,

If you have a good difference in terms of boiling point, distill your product. 

Trace amount of water can be removed by either

1. Dissolve it in an organic solvent and use Na2SO4 and then filter it.  OR

2. Pass it through a silica plug(5-10 g silica) using a solvent it is soluble it. Silica plug should get rid of acidic impurities as well.

Do you know what the acidic impurities are?

  dissolve it suitable solvent,   dry it over  anhydrous sodium sulphate or magnesium sulphate  than you can pass it over basic alumina to remove acidic impurities

 Dear Pratik,

I am not very sure on what acidic impurities are, but since I used Thionyl Chloride, so I believe that trace amount of HCl might be there or may some other chlorides.

If you are facing a huge amount of degradation during silica plug, I would suggest you using the product directly for the next step. What is your next step in the reaction?

Maybe you don't have to do aqueous work up at all for your reaction. Use thionyl chloride with a little DMF or pyridine as catalyst. Once reaction is complete remove all the volatiles including excess thionyl chloride with a good vacuum (sometimes good to use a solvent higher boiling than thionyl to get it all out), Dissolve crude product in suitable inert solvent and pass through a silica or alumina plug to remove any amine hydrochlorides.

Dear Richard,

Your answer is really appreciated. Many thanks. I will surely try with this idea.

Thanks