At the current rate of the anime...

[artondrius]

So recently the anime has been covering exactly 2 chapters per episode. If they keep going at that pace, here is how far they will get by the end of the year. (note this is only hypothetical, the pace could change at any time).

November 07 / Ep. 337 / Chapter 585-586 (Izanami activates) *this episode is already confirmed
November 14 / Ep. 338 / Chapter 587-588 (More Izanami stuff & 5 Kage vs Madara)
November 21 / Ep. 339 / Chapter 589-590 (Edo Tensei released)
November 28 / Ep. 340 / Chapter 591-592 (Madara frees himself, Taka/Orochimaru stuff)
December 05 / Ep. 341 / Chapter 593-594 (Taka/Orochimaru stuff, and back to the Tobi fight)
December 12 / Ep. 342 / Chapter 595-596 (More Tobi fight)
[December 19 / Ep. 343 / Chapter 597-598 (More Tobi fight, mask breaks at the end)
December 26 / There is usually no episode on the last week of the year

So I think it's very likely we will see Tobi's mask break by the end of December in the anime.

 

[Itachi Edo]

I hope so, but I hope not as well. I'm not saying I want random fillers, but that would put it way too close to the manga.

 

[vasu 32]

well whatever,we aren't going to get fillers anymore either way as confirmed by hayate date,or whatever,and they already completed till chapter 607 fully after which there is a 0.8 probability of getting a break for 7 weeks or months and probability of 0.2 to get special episodes,no alteration of storyline ep.