$re = '~(?s)(?:START).*?(?:END)(?-s)|//.+|\. old|^\s+old(*SKIP)(*FAIL)|\b(old)\b~m';
$str = 'xx START xx old xx END xx --> ignore
xx old xx --> REPLACE !
START xx old --> ignore
xx old xx END --> ignore
xx old xx --> REPLACE !
// xx old --> ignore
xx // xx old --> ignore
xx . old old xx --> ignore first one, replace second one
.
old --> ignore
(old) xx --> REPLACE !
xx old xx --> REPLACE !';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
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