Come up with a synthetic method to convert benzene to 1-phenyl-2-?

Question

I meant to ask Come up with a synthetic method to convert benzene to 1-phenyl-2-bromoethane.

Answer 1

Use 1-chloro-2-hydroxyethanone with benzene (using aluminum chloride as a catalyst) to accomplish the alkanolyation. Then, change the hydroxyl group into a bromine using phosphorous tribromide. Finally, do catalytic hydrogenation to remove the carbonyl group. There you go.

Alternatively, but less selectively you might just do a friedel krafts alkylation with 1,2-dibromoethane (and aluminum chloride and benzene). However, this is less effective than other options since multiple alkylations and cross-linking of benzenes are likely.

Answer 2

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