IPhone 3GS is hanging each time I try to sync with iTunes

We're running the latest version of iTunes and the iPhone software is up to date.
I have an iMac and my son wanted his own "library" of music, so under his user name, we've loaded new music into iTunes.  Plugged his phone in to sync to the new music and can't get past "Transferring Purchases from ...... phone" or if we do get past it, we can only get to Step 2 and it hangs there.
So, it's really hanging in two different places.
I've tried a hard restart on my Mac and that did nothing.
I've tried a force quit on iTunes numerous times.
Nothing appears to work.
Anyone have any ideas?

Well reading some other discussions i have found to try deauthirizing and reauthorizing, that didn't work. I guess i could remove iTunes and reinstall, but i hate to do that. Maybe I should take all the music off and sync and then try putting  it back on? Worked before i put music on there, but then there wasn't much to sync at that time. Anyone know of other possible causes that would make iTunes stop working?

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