If he is in fact grandfathered for 245(i), then yes.
You should retain an experienced immigration lawyer to review all the facts, advise you, and handle the case. You can find one through http://www.ailalawyer.com.
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Generally, yes - but in addition to making sure he really is grandfathered, you need to make sure no bars apply that 245(i) does not waive. For example: if he left the US at some point he may be subject to a departure bar that 245(i) does not waive. I suggest discussing the details with an attorney. Good luck!
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Maybe. However, you need to reatain an experienced Immigration Attorney for assistance.
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He should be able to adjust under 245(I).
The above is intended only as general information, and does not constitute legal advice. You must speak with an attorney to discuss your individual case.