re = /((?:^|\.)(?=[^.]*(?:saturday|sunday|weekend))[^.]*)brunch/i
str = 'Limit 1 per person. Limit 1 per table. Not valid for carryout. Not valid with any other offers, no cash back. Valid only for Wednesday-Friday dinner and Saturday-Sunday brunch. Not valid on federal holidays. Reservation required.
Weekend brunch brunch.'
subst = '\\1BRUNCH'
result = str.gsub(re, subst)
# Print the result of the substitution
puts 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 Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html