This is a starightoward requirement to implement in JIRA.
You have the add a validation on the transition which is taking the ticket to "re-open status". Basically in the workflow configuration you can add "comments screen" on the trasition such that a comment box appears when transition is to the re-opn status and also add a validation that the comments box should be filled otherwise the transition will fail.
I will suggest to you to use the comments box rather an custom field called "reason"
You can also use the plugin script runner for the same purpose.
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