Why does it say "b'Chalev Efrasah"?
'Rashi': He called the city Efrasah due to his wife.
Radak citing Meforshim: the city was called so after Kalev and his wife. If so, Chetzron entered Eretz Yisrael and died there 1 .
Radak: Chetzron died at the time that his son Kalev married Efrasah.
Malbim: The prefix Beis refers to time. At [about] the time that Kalev married Efrasah (19), Chetzron married Aviyah, and he died (shortly after). The Beis also means with - Kalev and Efrasah raised Aschur, so it is as if they gave birth to him together with Aviyah.
Radak: This is difficult, to say that he lived more than 250 years! (Why did he not ask that the only Yisraelim who left Egypt and entered the land were Kalev and Yehoshua? Some say that there was no decree on men who left Egypt above 60 years. - PF)
When did she give birth to Aschur?
'Rashi': After Chetzron died. Malbim - the Sefer teaches this, for Kalev and his wife Efrasah raised the orphan Aschur. Aschur was considered Ben Kalev, and is listed below (4:4-5) with Chor, the son of Kalev and Efrasah. "Asher Yaldah l'Adri'el" - because he raised them, they are ca111ed on his name 1 (Sanhedrin 19b).
Radak: It could be in his lifetime 2 , or after his death. Chetzron married Bas Machir when he was 60; here informs that he married another wife Aviyah.
Who was Teko'a?
'Rashi': The officer of the city Teko'a.
