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Good find, but: it will run 9 external commands and thus use approx. the fivefold time, and, as is, it won't confine itself on .doc[x]? and .pdf files.

That was not mentioned in your OP. Try
find SRC -iname "*.doc*" | while read FP; do FB="${FP%.*}"; [ ! -f "${FB/SRC/DST}.pdf" ] && echo "$FP"; done
SRC/D2/File6.doc
SRC/D2/File2.docx...

Did you ever try to run that line?


Try instead

cd SRC; for FN in *.doc*; do [ ! -f ../DST/${FN%.*}.pdf ] && echo $FN; done; cd ..
File2.docx
File6.doc

Any attempts / ideas / thoughts form your side?