Copy Multiple Files To Multiple Directories Simultaneously: jMultiFilesAndDirsCopy
jMultiFilesAndDirsCopy is portable application that helps copy multiple files to multiple directories. It also offers support for overwriting similar files or skipping these files, depending on the settings you choose. An automatic log of all copied files is created, allowing you to view file copying history when you want.
It is a Java-based application. From the main interface, click Choose a File and navigate to the file you want to copy. Click Add the File button to add the selected files to the application. Select the directory to which you want to copy selected files by clicking on Choose a Dir button. Check options for file overwriting or skipping similar files from the top if Matching: options. Click Copy src to copy the selected files to the designated folders.
Link: jMultiFilesAndDirsCopy by Alessandro Basso
The download is a ZIP file which contains the application [portable] and a 7 page PDF [application handbook]
Tested on Windows 7.