2c-b -> dob ?

[Vaaguh]

Do you guys think this would work ?

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000366927-file_nfh2.jpg" title="View this image">

I am not sure if the Al/Hg will reduce the alkene producing a decent yield, should I consider using NaBH4 and Al/Hg for reducing ?

[Rhodium]

The dehydration of the intermediate nitroalkohol to the nitroalkene won't happen without vigorous conditions, such as heating with phtalic anhydride, as the alkene isn't conjugated with the benzene ring. That step alone will be so low-yielding that the synthesis is of no use.

Start from scratch, that is much more plausible than this suggestion.
Alcohol, an unconsciousness-expanding drug

[No1CockSucker]

2C-B + potassium permanganate --> 4-bromo-2,5-dimethoxy-benzoic acid.