My iPhone had (has) this weird problem during its sync process. Somehow my bookmark changes don’t get transfered to the iPhone. I always encounter some old bookmarks. And yes, I tried ticking the “Replace Bookmarks on next sync” option in iTunes without success.
The solution is to sync the Bookmarks.plist file out of ∼/Library/Safari/ manually to your ∼/Library/Safari/ on the iPhone, reboot and off you go. Perhaps you want to remove the Bookmarks Menu and Bookmarks Bar by editing the .plist file.
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iphone bookmarks sync problem
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