Drag and drop file to specific target

I have a set of elements of media files listed like this.

I want to upload a a media file from windows explorer to a specific target of this list(for eg- It should be possible to add file above 'Title A' or below 'Title A'... ). How to achieve this?I know how to upload a file and it is achievable for me if it's to add to the end of the list. What I don't get is how to get that specific position which I need to upload.

(If it's a DOM element, I could have used jQuery draggable droppble, but again it's not possible here! :(. )

Any help?!

Thank you.