Wordpress - How to add a shortcode button to the TinyMCE editor?

To add our button to the TinyMCE editor we need to do several things:

1. Add our button to the toolbar
2. Register a TinyMCE plugin
3. Create that TinyMCE plug-in which tells TinyMCE what to do when our button is clicked.

Steps #1 and #2

In these steps we register our TinyMCE plug-in which will live inside a javascript file at 'path/to/shortcode.js' (see wpse72394_register_tinymce_plugin() below)

 // init process for registering our button
 add_action('init', 'wpse72394_shortcode_button_init');
 function wpse72394_shortcode_button_init() {

      //Abort early if the user will never see TinyMCE
      if ( ! current_user_can('edit_posts') && ! current_user_can('edit_pages') && get_user_option('rich_editing') == 'true')
           return;

      //Add a callback to regiser our tinymce plugin   
      add_filter("mce_external_plugins", "wpse72394_register_tinymce_plugin"); 

      // Add a callback to add our button to the TinyMCE toolbar
      add_filter('mce_buttons', 'wpse72394_add_tinymce_button');
}


//This callback registers our plug-in
function wpse72394_register_tinymce_plugin($plugin_array) {
    $plugin_array['wpse72394_button'] = 'path/to/shortcode.js';
    return $plugin_array;
}

//This callback adds our button to the toolbar
function wpse72394_add_tinymce_button($buttons) {
            //Add the button ID to the $button array
    $buttons[] = "wpse72394_button";
    return $buttons;
}

Step #3

Now we need to create our TinyMCE plug-in. This will go in a file 'path/to/shortcode.js' (as specified in the early steps).

jQuery(document).ready(function($) {

    tinymce.create('tinymce.plugins.wpse72394_plugin', {
        init : function(ed, url) {
                // Register command for when button is clicked
                ed.addCommand('wpse72394_insert_shortcode', function() {
                    selected = tinyMCE.activeEditor.selection.getContent();

                    if( selected ){
                        //If text is selected when button is clicked
                        //Wrap shortcode around it.
                        content =  '[shortcode]'+selected+'[/shortcode]';
                    }else{
                        content =  '[shortcode]';
                    }

                    tinymce.execCommand('mceInsertContent', false, content);
                });

            // Register buttons - trigger above command when clicked
            ed.addButton('wpse72394_button', {title : 'Insert shortcode', cmd : 'wpse72394_insert_shortcode', image: url + '/path/to/image.png' });
        },   
    });

    // Register our TinyMCE plugin
    // first parameter is the button ID1
    // second parameter must match the first parameter of the tinymce.create() function above
    tinymce.PluginManager.add('wpse72394_button', tinymce.plugins.wpse72394_plugin);
});

There's too much to put the whole answer here so checkout this guide: http://wp.smashingmagazine.com/2012/05/01/wordpress-shortcodes-complete-guide/

You have to create a Javascript file that takes action from the button you register through WordPress that inserts the TinyMCE button into the editor.