allylbenzene byzantine

[obituary]

This proposed synth is not supposed to be a well... efficient or in good yeilds, just a proposal to see if it is possible. 

Styrene + Br2/CCl4 --> 1,2-dibromophenylethane (A)
A + 2NaNH2/NH3 --> phenylacetylene (B)
B + NaH or NaNH2 --> sodium phenylacetylide (C)
C + MeI --> allylbenzene 

definitely long winded for the product, but just a fun idea.

[Rhodium]

Why would the initially formed Ph-CC-CH3 rearrange to Ph-CH2-CH=CH2? Am I overlooking something?

[obituary]

ooops, meant propenyl benzene, not allylbenzene.
sorry the idea came very late last night.

[Rhodium]

I still think you will end up with propynylbenzene, not propenylbenzene. Propynylbenzene is Ph-CC-CH3 with a triple bond in the middle, not a double bond as in propenylbenzene.

[obituary]

you're correct again, sorry about the confusion- still with a hydrogenation procedure, you could get the allylbenzene- keep in mind obit isn't after yeild here.

[obituary]

is it possible to take the
propynylbenzene + 2HX --> gem dihalide, 
then gem. dihalide + OH^- --> gem. diol
which will automatically lose water to give the ketone, P2P.  (and Phenyl ethyl ketone)