High Bees!
The following post by Lego has sparked my interest:
Post 464635 (missing)
(Lego: "P2P from bromobenzene/CuI/Acetylacetone", Methods Discourse). Obvisouly this means that the ideas has to be tested on various interesting substrates. The first compound i have chosen to test is 5-bromo-1,3-benzodioxole to MDP2P.
As the substrate is a bromo substituted halide and not a iodo substitudedhalide, the reactiontime is about 30 hrs. This means that the results from the reaction wont be presented untill monday (i dont have internet at home yet - so I can post before that). This is what happened anyway:
The following reagents/solvents where used:
500 mL DMSO (99%+ purity)
3,8 g / 20 mmole CuI (99,999%+ purity )
8,5 g Na2CO3/ 80 mmole (99%+ purity)
40 g / 0,4 mole AcetylAcetone (99%+ purity)
40 g 5-bromo-1,3-benzodioxole / 200 mmole (97%+ purity)The DMSO was placed in a 2 L RBF and put in an oil bath. CuI was added in one portion. This caused the solvent to take on a beautiful green color. Immediately after Na
2CO
3 was added. The color switced to a pale opaque green. Acetylacetone was then poured into the mixture. This caused quite a spectacular reaction. Immediately the mixture turned very deeply green and after 10 seconds it turned bloody-red. After one minute the 5-bromo-1,3-benzodioxole was added. This caused the solution to turn even more deeply red. The whole shebang was submerged in an oilbath and stirring was commensed at 120
oC.
The workup will be commensed tomorrow morning. Hopefully it'll give some nice results
.
Finally i have a few questions regarding the workup. The article says that the deacetylation can be done in the same pot as the reaction. Exactly what does this mean? Should i simply add the NaOH mixture once the reaction is done? Or do they extract the mixture first and then treat the crude reaction with NaOH? Finally, how dilute should the NaOH mixture be, and how much is to be used?
I'll follow the thread up with results. Just got access to GC-MS and HPLC-MS, so i'll analyse whatever comes out of the porrage
The following substrates will also be tested once the schedule time is right:
Iodobenzene
2,5-dimethoxybromobenzene
p-isopropoxy-bromobenzeneRegards
Bandil