The regiochemistry of the alcohol would be wrong with the hydroboration/oxidation thing.
There are several problems with your proposal, right of the bat I don't believe that a grinard reagent can be formed with bromobenzene.gravenewworld said:Here is another way I thought of to synthesize your desired compound:
1) Turn bromobeneze into a grignard reagent by the usual methods. Put it aside.
2.) Do a hydroboration oxidation on the terminal alkene to create the primary alcohol.
3) Do a swern oxidation on the primary alcohol to create the aldehyde.
4). React the created grignard reagent with the aldehyde and then add some acid. Your result will be your desired product.
Again, not very plausible, similar reasoning as above.How about epoxidation of the alkene with MCPBA, then make the Gilman reagent of the bromobenzene (nBuLi, then CuI). Mixing that with the epoxide should open the epoxide at the less hindered position and give the right regiochemistry.