I don't know how stable the ketone chain would be under steps 4 and 5.
It will not survive intact, but if you make the ethylene glycol ketal of the ketone first it can take the abuse of step 4/5, and then you can deprotect it afterwards.
This general procedure is described as steps F & G in Fig 1 of http://journal.kcsnet.or.kr/publi/bul/bu99n12/1517.pdf (http://journal.kcsnet.or.kr/publi/bul/bu99n12/1517.pdf)
and can easily be adapted to this molecule. Ketals are stable towards halogens and bases, but are hydrolyzed to the ketone again by aqueous acid.
You mioght also want to look at this article (also see the pictures in the PDF, as they help a lot): Post 479459 (https://www.thevespiary.org/talk/index.php?topic=11483.msg47945900#msg47945900)
(GC_MS: "Novel syntheses related to asarone", Novel Discourse)
Rhodium, you are really a wonder! That protection mechanism is very simple, and OTC. The acid sensitivity of the protected group will make the isolation of the intermediate phenol slightly more difficult (can't simply add HCl and filter :P ), but everything else should be really straightforward. Thanks a lot! :)
Addendum: The p-toluenesulfonic acid catalyst can be prepared easily from toluene and sulfuric acid. See Post 462272 (https://www.thevespiary.org/talk/index.php?topic=7226.msg46227200#msg46227200)
(roger2003: "Alkylbenzenesulfonic Acids", Chemistry Discourse), Post 389646 (https://www.thevespiary.org/talk/index.php?topic=9366.msg38964600#msg38964600)
(Antoncho: "Toluenesulfonic acid - tips and tricks.", Methods Discourse), and Post 261000 (https://www.thevespiary.org/talk/index.php?topic=6776.msg26100000#msg26100000)
(Chromic: "p-toluenesulfonic acid", Chemistry Discourse).
Also, I would prefer that SWIM not have to deal with elemental bromine, but in situ bromine generation requires acidic conditions with a strong oxidizer present. Would something like NaI/I2 selectively halogenate the 2-position as well?