Typically, when I have a situation where the jamb is wider than the wall's thickness, I push the brick moulding against the exterior wall and make a filler to space the interior casing to match the jamb width.
BUT
Sometimes, the interior just won't look right if the jamb doesn't sit flush with the walls. In this case, a filler behind the exterior brick moulding is the way to go. Caulk the filler, front and back, as if you're trying to glue it on and it should be a weather-tight seal.
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