I'm trying to make more room on my phone by deleting most of my songs and just keeping a few playlists.

But when i try to sync my phone in itunes it won't let me because i don't have enough storage left on my iphone 5!!!
How do i get around this catch 22? My son has a similar problem with his iphone4, except that he deleted everything off his phone (photos and songs) and still doesnt have enough room to take a picture!
Thanks, any help would be appreciated.

Deleting a playlist will not remove the songs and make any space on your phone.  It sounds like you have iTunes match enabled, meaning that your playlists are synch'd across all of your devices.  If you deleted the playlist it is gone and you will have to build it again. the only way to free up music space on the iPhone is to delete the songs themselves from the songs list.

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