I want procedure of reaction of 1,2 dibromoethane with a primary amine.
what is your desired product? The monoalkylated, dialkylated, cyclic product? Generally it is difficult to stop at the monoalkylation of a primary amine. If the monoalkylation is the desired product, it is better to do reductive animation with chloroacetaldehyde.
In dibromo compound, I want amination at one bromine and I want another bromine molecule free
Use 2-2.5 eq of dibromoethane. Do the reaction in mild conditions, like ice cold. Slow dropwise addition of dibromoethane to solution of your amine should work. Do the dropwise addition very slowly using a dropper.
I think it will be better to attach the bromo side first prior to the amine. The unprotected amine can react with the halide to form an azetine.
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3423225/
The acetal protected bromo compound is available, or you can use 2-bromoethanol.
https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0034-1381164.pdf
@Harshit
Is your amine aliphatic or aromatic? Primary aliphatic amines are very nucleophilic. You most probably would not need a catalyst. I usually use ethanol as solvent for my nucleophilic substitution reactions.
Hai. Try the following condition:
sodium methoxide-1.2 eq
Methanol: 6 volume
1,2-dibromoethane-7.5 eq. stir for 6-7 hrs or monitor by TLC.
And also
Instead of sodium methoxide use Potassium carbonate, sodium hydroxide and DBU.
excee 1,2-dibromo ethane must be distilled out.
work up: Add water and stir then allow layers to separate. Bottom layer is your product layer. distill out excess 1,2-dibromo ethane.
Add IPA (2.0 Vol) to the reaction residue then reflux and bring to RT. stir with n-hexane (5.0 Vol) to get your product if solid.
Best of luck
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