Itachi Pursuit Mission

The Hunt for Itachi is a story arc from Part II of the Naruto series that spans from chapters 343 to 402. It is typically further divided into a number of smaller arcs.

Summary
Sasuke betrays and defeats Orochimaru, feeling that he can learn nothing else from him and that Orochimaru is unworthy of having his body. Although Orochimaru attempts to take his body by force, Sasuke is able to turn the process against him, later reporting to have simply retained control of his body and absorbing his master. With Orochimaru gone, Sasuke recruits Suigetsu, Karin, and Jugo, former subordinates and/or experimental subjects of Orochimaru, to help him in finding and ultimately killing Itachi. After naming their group "Hebi", the group sets out to find their target. Tsunade hears of this and assembles Team Kakashi and Team 8, that together makes the Eight Man Squad. They are set out to capture Itachi and intercept Sasuke.

Sasuke ends up fighting and defeating Deidara, who dies by using a jutsu that sacrifices his own life in the form of a huge explosion. Sasuke summons the snake Manda to use him as a shield against the explosion.

After learning of an Akatsuki lair nearby, they go to investigate. Here, after going in alone, Sasuke finds Itachi. After a brief scuffle Itachi remarks how much Sasuke has grown, and then tells Sasuke to meet him at the Uchiha hideout so that they can finish their dispute.

Meanwhile, Jiraiya discusses with one of the Toads on how Naruto may soon need to completely remove the sealing of the fox. Jiraiya states this because he feels he may soon die after fighting Pain. He makes it far into a long drawn out battle, but dies after falling to Pain. However, he does not die before revealing the truth of Pain through a code he writes on the back of an elder toad. This message is quickly delivered to Tsunade.

Sasuke and his companions Taka, are en route to the Uchiha hideout when Itachi's partner, Kisame, appears in front of them. He insists that Sasuke keeps the deal with his brother and travels on on his own to meet Itachi alone. This suits Sasuke and Suigetsu fine, as Suigetsu wishes to challenge Kisame for his Samehada, and Sasuke would insist on fighting Itachi alone. Sasuke and Itachi fight in a bloody duel of fates. During the battle, Itachi vomits blood. This is because of an unknown disease, or as stated by Zetsu, "I wouldn't be surprised if Itachi sustained some sever damage before the battle started". At the end of the fight Itachi dies while giving Sasuke a last poke on the forehead. Here Itachi says "Sasuke... there won't be a next time" before collapsing, referring to all the times he has told his little brother that he will spend time with him another time.