Im am attempting a synthesis of an organic lignand which has 4,6 Benzhydrl-5-amino-cumene as its main constituent. My plan to synthesize this compound
is by brominating 5-isopropyl-resorcinol to 4,6 bromocumene and then nitrating it to 4,6-bromo-5-nitro-cumene. Then react that with Mg to form a
gringard reagent, and use a Kumada coupling reaction between it and bromodiphenylmethane to form 4,6-benzhydrl-5-nitro-cumene. Then the nitro group
would be reduced to a amine using PtO2.
Does this synth seem like it would work? I also am only going to try it if I can find a way to make 5-isopropylresorcinol or if my inquiry about its
price is something I can afford.
Is there anything you guys can find on a synth for 5-isopropylresorcinol? I cant really find anything. Could I use a Friedel-Crafts Alkylation with
resorcinol's methyl ester and isopropyl chloride to form it?
after this you can do kumada coupling followed by reduction to get the target compound
Jackson - 24-1-2019 at 08:10
Okay, thanks so much.
So the nitration will favor the 5 position?
I assume so but I just want to make sure.
Thanks,
JacksonJackson - 24-1-2019 at 10:11
CuReUS
For the first reaction, I cannot find how that paper has any mention of creating a methyl resorcinol from resorcinol. I must be missing something,
could you tell me what you are refering too?
For the first reaction, I cannot find how that paper has any mention of creating a methyl resorcinol from resorcinol. Jackson
Sorry I made a mistake.The paper uses m-cresol,not resorcinol.I mistook the methyl group of m-cresol for OH .This means we can't make 5-isopropyl resorcinol that way
the another thing you could do is to make 3,5-dihydroxybenzoic acid(from resorcinol or benzoic acid),do a kochi reaction to get 5-bromoresorcinol and
then do a suzuki coupling with 2-bromopropane to get 5-isopropylresorcinol
.This means we can't make 5-isopropyl resorcinol that way