I think that in your case it must made freidelcraft,s reaction with suitable anhydride  under F.C. reaction condition followed by specific reduction

You might be able to adapt the following reaction:

Strategies toward improving the brain penetration of macrocyclic tertiary carbinamine BACE-1 inhibitors

Keith P. Moore; Hong Zhu; Hemaka A. Rajapakse; et al

Bioorganic & Medicinal Chemistry Letters 17 (2007) 5831–5835

  Picture shows: meta-Bromo-alanine, protected  as NHBOc and Me ester.

Scheme 2. Reagents: (a) 9-BBN, NaOH, (Ph3P)4Pd, + but-3-en-1-yloxy t-butyldimethyl silane, 68%; (b) TBAF, THF, 99%;

You can brominate phenylalanine to get a mixture of the ortho (36%) and para(58%)-bromo derivatives. Either will react as shown above.

Chemistry of unprotected amino acids in aqueous solution: direct bromination of aromatic amino acids with bromoisocyanuric acid sodium salt under strong acidic condition

Yokoyama, Yuusaku; Yamaguchi, Tomotsugu; Sato, Masanori; Kobayashi, Eri; Murakami, Yasuoki; Okuno, Hiroaki

Chemical & Pharmaceutical Bulletin (2006), 54(12), 1715-1719

Bromination of unprotected arom. amino acids such as phenylalanine, tyrosine, and glycine, with bromoisocyanuric acid mono sodium salt (BICA-Na) was conducted in 60% aq. H2SO4 at 0° to give a mixt. of mono-brominated products in good yield. Unexpectedly, meta-bromophenylglycine was obtained as main product accompanied by ortho- and para-substituted products, while phenylalanine gave only ortho- and para-substituted products. Bromination of 2-phenylethylamine or benzylamine showed a tendency similar to the corresponding amino acids.

You might have to protect the amine and/or the COOH group during the reaction with BBN.

After you have added a 5-carbon alcohol chain, oxidize it to the aldehyde.