[Altered State]

Hello.

I need to draw a mechanism to prepare the product you can see in the image bellow, only using benzene, any alifatic compound with 3 or less Carbon atoms and any inorganic reactant.

I think the mechanism is right, I need you to confirm that.
I have doubts about bromination. Will it occur in that possition? And why? In what yield?

I would like to know alternative ways of doing this exercise, easier or with greater yields. Any help is well recived.

So this is it:

[Altered State]

Any thoughts?
I need it for tomorrow evening

[Altered State]

Please, I really need some help here, if there is anything that is not clear so you can't answer me, please, let me know.
It's obvious I've already attemted my exercise, in fact, I've already make it, but I can't explain why the bromination step occurs in that position, and even if it occurs.
I wanna know some other methods and mechanisms to get the product.
Regards!

[discodermolide]

Bromination should go in the benzylic position.
Then you are making a phosphonium salt to do a Wittig reaction, from there to the diol and what looks like a pinacol rearrangement.
I don't see why that route would not work.

[Archer]

Have you considered any other ways of preparing alkyl halides? Maybe think about the use of PBr₃ on certain substrates which would be available from propiophenone.

[Dan]

You might be able to do a pinacol coupling with the ketone from your F-C acylation (ethyl phenyl ketone) to cut out a few steps.

[orgopete]

You might be able to do a pinacol coupling with the ketone from your F-C acylation (ethyl phenyl ketone) to cut out a few steps.

I agree with this suggestion. What I was uncertain about is whether this reaction was covered in the poster's textbook.

[Altered State]

You might be able to do a pinacol coupling with the ketone from your F-C acylation (ethyl phenyl ketone) to cut out a few steps.

I agree with this suggestion. What I was uncertain about is whether this reaction was covered in the poster's textbook.

It is not covered in my course, but I've researched a bit about this pinacol coupling and just discovered that I can do in 2 steps what I have done in about 8 steps...
I'm going to do and learn the exercise both ways, really nice reaction you just discovered me.

Thank you all again.