FrankenNeko

Going on one hour of sleep is really starting to affect me...

I know carboxyl have a carbonyl group and a hyroxyl group.... I am thinking I need to do an FGI and from there I can break up the molecule into two. 4-Fluorophenethyl alcohol is commercially available 4-Bromobenzaldehyde is also commercially available, but i'm still unsure how to put those two together...

That attached thumbnail is extremely helpful. I was going about it all the wrong way. As for making alkyl bonds to benzene rings, i believe i will have to do a synthesis of nitrobenzene and aniline in order to get the F attached to the benzene. And you use an electrophilic substitution reaction between benzene and bromine. My thoughts are the next disconnect is at the carboxylic acid RCOOH Or what do you think about doing a functional group interconversion to give the ester form of the carboxylic acid?

So far I have H2C=C=O + benzyl alcohol -----> benzyl acetate which is the left hand side of the molecule. Is this correct? The next part is the part that is confusing me most. I'm not sure how to put those two benzene rings together in that way.

I have to go to work right now but will get right back at this when I get home. I know there is the ester bond smack dab in the middle. I will work form there! Unless I'm wrong.... Is there a more obvious starting point?

How would I perform a retrosynthesis on this molecule? The starting material should be commercially available. Any idea on how many steps it would take?