Regular Expressions 101

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/
(?:[a-z]\))?([+?\s\S])(?:<br\s*\/>\s*)?(?=[{1}a-z]\)|$)
/
g
Non-capturing group
(?:[a-z]\))?
? matches the previous token between zero and one times, as many times as possible, giving back as needed (greedy)
Match a single character present in the list below
[a-z]
a-z matches a single character in the range between a (index 97) and z (index 122) (case sensitive)
\) matches the character ) literally (case sensitive)
1st Capturing Group
([+?\s\S])
Match a single character present in the list below
[\s\S]
+? matches the previous token between one and unlimited times, as few times as possible, expanding as needed (lazy)
\s matches any whitespace character (equivalent to [\r\n\t\f\v \u00a0\u1680\u2000-\u200a\u2028\u2029\u202f\u205f\u3000\ufeff])
\S matches any non-whitespace character (equivalent to [^\r\n\t\f\v \u00a0\u1680\u2000-\u200a\u2028\u2029\u202f\u205f\u3000\ufeff])
Non-capturing group
(?:<br\s*\/>\s*)?
? matches the previous token between zero and one times, as many times as possible, giving back as needed (greedy)
<br matches the characters <br literally (case sensitive)
\s
matches any whitespace character (equivalent to [\r\n\t\f\v \u00a0\u1680\u2000-\u200a\u2028\u2029\u202f\u205f\u3000\ufeff])
* matches the previous token between zero and unlimited times, as many times as possible, giving back as needed (greedy)
\/ matches the character / literally (case sensitive)
> matches the character > literally (case sensitive)
\s
matches any whitespace character (equivalent to [\r\n\t\f\v \u00a0\u1680\u2000-\u200a\u2028\u2029\u202f\u205f\u3000\ufeff])
Positive Lookahead
(?=[{1}a-z]\)|$)
Assert that the Regex below matches
1st Alternative
[{1}a-z]\)
Match a single character present in the list below
[a-z]
{1} matches the previous token exactly one time (meaningless quantifier)
a-z matches a single character in the range between a (index 97) and z (index 122) (case sensitive)
\) matches the character ) literally (case sensitive)
2nd Alternative
$
$ asserts position at the end of the string
Global pattern flags
g modifier: global. All matches (don't return after first match)
Your regular expression does not match the subject string.

Regular Expression
No Match

/
/
g

Test String