use strict;
my $str = '__DATA__
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 !';
my $regex = qr/(?:(?s:START.*?END)|\/\/.*|\.\s*\w+\b)(*SKIP)(*F)|old/p;
my $subst = 'new';
my $result = $str =~ s/$regex/$subst/rg;
print "The result of the substitution is' $result\n";
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 Perl, please visit: http://perldoc.perl.org/perlre.html