I am trying the hypothetical synthesis below, but I didn't get the product I was expecting. Instead, the reaction formed mostly styrene, in >80% yield (elimination product of the bromide)
The synthesis of an analogous product with one less carbon in the bromide (benzylic bromide) is described in the literature and I thought it would work with this one since they only differ by a carbon. Any thoughts on how I could overcome this selectivity problem?
I thought about using a milder base, but I don't think the problem here is actually the base I use, cause they will all form the enolate, the problem is the enolate abstracting the benzylic proton from the bromide and generating styrene + butyrolactone.