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Assuming that you are trying to send the book to iBooks on your iPhone, have you done a "connect to iTunes" before trying the Send to Device?
Just for interest if you started with Word, why did you go through the PDF stage? PDF is notoriously difficult to do a good conversion on. If starting with Word the best results are normally achieved by using the Save As Web Page (filtered) option and then loVing that into calibre for the conversion to ePub.
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