Yosef is sent by his father to Shechem with a few tasks. Rabbi Mordechai Breuer divided Yosef’s mission to his brothers: See how they are, how the sheep are, and return to me with the update.
As his brothers are no longer in Shechem, only the first is partially achieved, and Yosef never returns after he is sold to Egypt. Malbim and Rashbam credit Yosef for seeking them beyond Shechem. Yaakov had made Yosef a “shaliach l’dvar mitzvah” (an agent for fulfilling a mitzvah) which would protect him in both directions. Or Hachaim and Beit Halevi note that once he went to Dotan he was no longer under the protection of his father’s command, and that is where the story turned sour for him.
Rabbi Breuer suggests that Shechem was not on the same crossroad that would have allowed the brothers to see the traveling caravans, so their location shift was not accidental, as it meant to set the stage for the national sojourn to Egypt.
After arriving in Shechem, Yosef is found by a “man” who notices him lost in a field and who tells Yosef that he heard the brothers say, “We shall go to Dotan.” Most people assume that Dotan is a geographical location a short distance from Shechem (Rashbam 37:17). But using a play on words, Rashi (37:17) raises the possibility that they went “to seek against you [Yosef] conspiracies of legal pretexts” to put you to death. As Rabbi Yoel Bin Nun argues, Yosef’s may later see this as a setup, a conspiracy against him.
What is the significance of Shechem, Dotan, the field and the “man” who finds him?
Many commentaries note that Shechem is a place set aside for difficult stories: Dinah, sale of Yosef, splitting of the kingdoms of Israel, and a place of murderers (Hoshea 6:9). If so, Yaakov sending Yosef there would seem to be poor judgment.
That the brothers were there may indicate the brothers’ independence. They were comfortable going back to where the Shimon and Levi massacre had taken place, to the city they had all plundered. Radak argues that their comfort level there made it seem as if nothing had ever happened.