Need to update iPhone3GS from iOS 3.1.3 to current

Need to update iPhone 3GS from iOS 3.1.3 to at least 6 or greater for any apps, etc. Phone has been out of commission for long time. Keep getting unknown error via MacBook iTunes syncing preventing update. Do I need to manually 'step up' upgrade to an old but newer than 3.1.3 version iOS? If yes, exactly how do I do this? Also, what minimum iOS version allows iMessaging? Thank you in advance for any assistance - Jill

UPDATING iOS
Over the air updating of iOS needs iOS 5 or later so unless you have iOS 5 or later you will not see updating in setting
The following link explains how to update http://support.apple.com/kb/HT4972
This link explains how to update using wireless http://support.apple.com/kb/HT4623
This explains how to transfer purchases to your computer http://support.apple.com/kb/ht1848

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