SO3H replacement with a halogen on a primary carbo

[amine]

Hi, I'm wondering if there is any established method for replacing a SO3H group with a Br/Cl halogen group or may be even completely eliminating it. (Mainly because of synthesis from taurine a very cheap amino acid..red bull it could give u more than just wings .

*that question 1


Also would doing a Friedel-Craft reaction on a dimethoxybenzene using a bromoethylamine work? (using AlBr3/AlCl3 to create a carbocation on the bromine end of the ring and attaching it).
*question 2.

Swim was looking at the article in the Novel Discourse section where Ethylenimide is run thru the same reaction(similar) and alkylation of the benzene ring occurs in 50% yield. Ethylenimide is a very carcinogen agent, recent studies show it is very effective at preventing viruses from replicating, they however show that bromoethylamine works well however not as dangerous as the ethylenimide.


Any help would be greatly appreciated.

[ning]

My book says:

If you react a sulfonic acid with PCl5 at high temperatures, it will become a halide. (yeah, right)

Hey, why don't you just make ethylene chlorohydrin and react it with an excess of ammonia, then HBr to give the desired 2-bromoethylamine? Note: antifreeze is much cheaper than taurine or PCl5.

I think the alkylation would work. No idea of yields.
You may wish to consider making 2,5-phenylmagnesium bromide grignard and reacting it with the above reagent as a substitute for F.C. alkylation.

[amine]

thx ning, question though, will the grignard work even though the with the amine present?

[Rhodium]

The most similar possible reaction is the alkylation of a protected aziridine with a grignard:

Post 184201

(Rhodium: "Ring opening of aziridine with PhMgX", Serious Chemistry)