const regex = new RegExp('(?<=\\w)(?<!\\w-\\w)(?: ?-+ ?)+(?=\\w)(?!\\w-\\w)', 'gm')
const 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>
`;
const subst = `—`;
// The substituted value will be contained in the result variable
const result = str.replace(regex, subst);
console.log('Substitution result: ', 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 JavaScript, please visit: https://developer.mozilla.org/en/docs/Web/JavaScript/Guide/Regular_Expressions