$re = '/(?<=\w)(?<!\w-\w)(?: ?-+ ?)+(?=\w)(?!\w-\w)/m';
$str = '<!-- The following should match. Not the dashes in the comment tag, obviously ;P -->
<h2 class="chapter_title">Chapter 01 -- The Beginning</h2>
<h2 class="chapter_title">Chapter 02 - The Reckoning</h2>
<h2 class="chapter_title">Chapter 03 - - The Aftermath</h2>
<h2 class="chapter_title">Chapter 04--The Conclusion</h2>
<p>I was having the usual - cheeseburger and a cold beer.</p>
<!-- The following should not match -->
<p>I was wearing a t-shirt.</p>
<p>It was a drunken mix-up</p>
<p>---</p>
<p>-----</p>
<p>- - -</p>
<p> - - </p>
<p> - - - </p>
';
$subst = "—";
$result = preg_replace($re, $subst, $str);
echo "The result of the substitution is ".$result;
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php