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NBS bromination of 2,4-dimethoxyphenylethylamine

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Vaaguh:
From a bottle that was labeled as "ricuarte's 2,4-dimethoxyphenylethylamine HCl" there was 5 gram (23 mmol) dissolved into 35 ml GAA.



To this mixture was added 4,9 gram (28 mmol) NBS which caused the solution to turn deeply red.



After covering the RBF with foil and placing a stopper on the flask the whole was stirred for 30 minutes. The precipated crystaline mass was filtered off and washed twice with ethyl acetate, another wash with H2O caused the solids to dissolve, the pH was adjusted to > 11 and the organic layer was extracted with 3x 30 ml EtO2, after removal of the solvents the residual oil was dissolved in 20 ml IPA and the solution was neutralized with dry HCl in IPA. The solids that formed where washed once with EtO2 and filtered to provide a crop of white crystals weighing 5,38 gram.

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An attemp to recrystalize the solids from IPA/Toluene (10ml ipa:5ml Toluene / gram) did not dissolve all sollids, even the addition of more IPA caused the solution to stay turbid. After allowing the solution to slowly cool down to RT the whole was refrigerated overnight providing 4,86 gram of what is beleived 4-bromo-2,4-dimethoxyphenylethylamine HCl (71 %)  with a mp of 235-237°C, a marquis reagent test gave a a dark green spot.

Captain_America:
...refrigerated overnight providing 4,86 gram of what is beleived 4-bromo-2,4-dimethoxyphenylethylamine HCl

Are you sure?  :P  :)

interesting work btw..

Vaaguh:

Are you sure?

--- End quote ---


There must have been mixed up a couple of 5's somewhere. ;)

Captain_America:
btw, what are you going to do with this compound? as I can see it can't yield anythig active w/o bost from MAOI.

Do you think that you can try this Post 518568 (Kinetic: "Iodination of arenes with KI and H2O2", Chemistry Discourse) on the 2,4-dimethoxyphenylethylamine and report back?

Vaaguh:
It was just a proof of concept.
More interesting substrates can be brominated in this friendly manner.

[edit (im seriously starting to go braindead with all those numbers) ]: Any idea what 5-iodo-2,4-dimethoxphenylethylamine would be like?

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