Preheat the oven to 400 degrees F. Line a baking sheet with parchment.
Bring the sugar and orange juice to a boil in a medium saucepan over medium-high heat and cook until the sugar has dissolved, about 3 minutes. Stir in the cranberries and 1 teaspoon rosemary and cook, stirring occasionally, until the liquid has thickened and reduced by half, about 20 minutes. Transfer to a baking sheet and refrigerate until cooled, about 1 hour.
Meanwhile, center the wheel of Brie on top of the bread boule. Using the Brie as a guide, trace a circle a little larger than the wheel of cheese with a paring knife and cut into the top of the bread and pull out the "plug". Trim and flatten it so it can be used as a lid for the bread bowl. Scoop out the insides of the bread boule, leaving about 1/2-inch of bread around the side.
Starting halfway up the side of the bread boule, use a serrated knife to cut a 1/2-inch deep horizontal slit around the entire bread boule. Now, starting at the rim of the bread boule cut down about 3/4-inch deep to connect to the first horizontal cut. Repeat all around the rim of the bread, spacing these vertical cuts about 1-inch apart. Brush the inside of the bread with the butter and sprinkle with the remaining 1 teaspoon rosemary, 1/2 teaspoon salt and a few grinds of pepper.
Reserve 1/4 cup of the cranberry sauce and spread the remaining sauce into the bottom of the bowl. Slice the top off the Brie and place into the bread on top of the cranberries. Transfer to the prepared baking sheet. Place the lid back on top and bake until the cheese is warm and gooey and the bread has turned a golden brown, 45 to 50 minutes.
Transfer to a serving platter and remove the lid and top with the reserved cranberry sauce. Rip the pull-apart pieces off around the outer edge and dip. Toast the extra scooped out bread and serve as extra dippers on the side.
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