I suspect that the problem is not with the replacement, but rather with the reading of the file itself. When I tried this the nieve way (using Word and copy-paste) I ended up with the same results as you, however examining content
showed that the .Net framework believe that the character was Unicode character 65533
, i.e. the "WTF?" character before the string replacement. You can check this yourself by examining the relevant character in the Visual Studio debugger, where it should show the character code:
content[0]; // 65533 '�'
The reason why the replace isn't working is simple - content
doesn't contain the string you gave it:
content.IndexOf("’"); // -1
As for why the file reading isn't working properly - you are probably using the wrong encoding when reading the file. (If no encoding is specified then the .Net framework will try to determine the correct encoding for you, however there is no 100% reliable way to do this and so often it can get it wrong). The exact encoding you need depends on the file itself, however in my case the encoding being used was Extended ASCII, and so to read the file I just needed to specify the correct encoding:
string content = File.ReadAllText(fileinfo.FullName, Encoding.GetEncoding("iso-8859-1"));
(See this question).
You also need to make sure that you specify the correct character in your replacement string - when using "odd" characters in code you may find it more reliable to specify the character by its character code, rather than as a string literal (which may cause problems if the encoding of the source file changes), for example the following worked for me:
content = content.Replace("\u0092", "'");