Hello ScarletRoxanne,

Here’s an approach which replaces each phrase/term with a temporary marker, then removes stopwords, then replaces the markers with their original terms:

use strict;
use warnings;
use Const::Fast;
use Data::Dump;

const my $DELIM => '\034';

my %stops =  map { lc $_ => 1 } qw( I am the of and you are );
my @terms =  ('manager of sales', 'chairman of the board');
   @terms =  sort { length $b <=> length $a } @terms;   # longest firs
+t
my $file3 = 'I am the Senior Manager of Sales and of Marketing. ' .
            'You are the Chairman of the Board of Directors.';
   $file3 =~ tr/A-Z/a-z/;               # convert to lower case

   # replace terms with temporary markers
   $file3 =~ s{$terms[$_]}{$DELIM$_$DELIM}gi for 0 .. $#terms;
my @file3 =  split /\s+/, $file3;
   @file3 =  grep { ! exists $stops{$_} } @file3;

for my $entry (@file3)
{
    if ($entry =~ /\Q$DELIM\E(\d+)\Q$DELIM\E/)
    {
        $entry = '*' . $terms[$1] . '*';
    }
    else
    {
        $entry =~ s{[[:punct:]]}{}g;    # remove punctuation
    }
}

print "$_\n" for @file3;
[download]

Output:

17:35 >perl 1997_SoPW.pl
senior
*manager of sales*
marketing
*chairman of the board*
directors

17:35 >
[download]

Hope that helps,