He fled with …: fled means “he escaped,” or “he left secretly in a hurry.”

All that he had: that is, “with everything he owned” or “with all his property.”

Arose and crossed the Euphrates: arose serves to put the focus on the action of the following verb. It may not need to be translated. See Good News Translation. For Euphrates see 2.14. The Hebrew text says “the river.” In 15.18 “the great river” is defined as “the Euphrates.” To the Hebrews “the river” meant the Euphrates river. From Haran, Laban’s home, to the Euphrates is a distance of about eighty kilometers (fifty miles).

Set his face is an idiom meaning “he headed toward,” “started toward,” “went in the direction of.”

Hill country of Gilead is a hilly territory east of the Jordan river in the northern part of modern Jordan. It is bounded roughly on the north by the Yarmuk river and on the south by the valley of Heshbon. See a biblical atlas. According to Num 32.1; Song 6.5, it was a good area for pasturing sheep, and so it was a logical destination for Jacob.

In translation the hill country of Gilead may be called, for example, “the hills called Gilead,” “the mountains named Gilead.” If neither hills nor mountains are known, translators may say “the region [area, land] called Gilead.” For further comments see verse 23.

Quoted with permission from Reyburn, William D. and Fry, Euan McG. A Handbook on Genesis. (UBS Helps for Translators). New York: UBS, 1997. For this and other handbooks for translators see here .