You'd need to break this down into a couple of steps
Your checkbox initial state should be disabled so the user can't simply click on it
http://www.htmlcodetutorial.com/forms/_INPUT_DISABLED.html[
^]
You then want to hook into the textbox 'onchange' event a have a function that validates the entry of the text box, making sure it's length > 0 or whatever your requirements are.
If it's OK, then enable the relevant checkbox and set it to checked.
In jQuery, this might read like
$(document).ready(function() {
$("#myTextBox").keyup(function() {
var isValid = $(this).val().length > 0;
$('#myCheckBoxItem').attr('checked', isValid )
});
});