I have attempted the formylation of the above mentioned compound using a very well reported protocol using secondary Butyl Lithium and TMEDA at - 78 degrees Celsius. I have done it quite a few times but did not see formation of the desired product either by LC-MS analysis or by TLC examination. I see mostly unreacted starting material in the TLC plate along with some minor spots (negligible). I have dried the TMEDA by refluxing in CaH2 and then distilling the TMEDA. The water content of DMF and THF (reaction solvent) has also been analyzed by using KF method. The procedure is very well reported in a lot of journal articles. However, I have been unable to get the product. When I used LDA instead of sec-BuLi as the base I could see very less formation of the desired aldehyde in the TLC which was isolated by column chromatography. The desired product just does not form.
Hello Arnab,
the following article might be helpful for you
Article Recent advances in N-formylation of amines and nitroarenes u...
all the best,
Sami
Dear Arnab Biswas please also see this useful article entitled
A Regioselective Synthesis of Dimethyl Phthalide-3-phosphonates
Article A Regioselective Synthesis of Dimethyl Phthalide-3-phosphonates
In the course o this work "Diethyl-2-formylbenzamides were regioselectively prepared by ortho lithiation-formylation of the corresponding benzamides."
Attached please see the general procedure.
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