YOU SAID:

My boss said he went to bed at 5:00pm.

INTO JAPANESE

私の上司は、彼が午後5時に寝ると言った。

BACK INTO ENGLISH

My boss said he would sleep at 5pm.

INTO JAPANESE

私の上司は、彼が午後5時に寝ると言った。

BACK INTO ENGLISH

My boss said he would sleep at 5pm.