For bromination, use Br2 in acetic acid & for iodination of an aromatic compd. use I2 in KI

Kumar,

Try two-phase hexane/solid N-halosuccinimide system which could be catalysed by the strongly acidic sulfonated resin Amberlyst® 15. See

---Yuri Goldberg, Howard Alper, Electrophilic halogenation of aromatics and heteroaromatics with N-halosuccinimides in a solid/liquid system using an H+ ion exchanger or ultrasonic irradiation, Journal of Molecular Catalysis 88, (1994) 377–383

Good luck

Kumar,

You may try Bis-(trifluoroacetoxy)iodobenzene — iodine system for iodination. see

--- Maurizio D'Auria, Giacomo Mauriello, Tetrahedron Letters 36 (1995)  4883–4884

Good luck

But I am worried about -TIPS. These halogenating reagents such as NBS, NIS or Br2 may also replace -TIPS by -Br/-I.

This reaction will not go well under standard electrophilic conditions. You will observe ipso substitution of the TIPS group which is significantly more activated due to the beta silicon effect.

You need to deprotonate the 2-position then add an electrophilic source of bromine at a low temperature. LDA at -78 C, warm to -40 C for 1hr, cool back down and add elemental bromine. If problematic, try other electrophilic bromine sources to quench the anion.

Dear Eric, thanks for your answer. I was also thinking to use BuLi or LDA followed by addition of CBr4/ I2.