Chocolate Babka

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3/4 cup warm milk (105–115°F)

1/2 cup plus 2 teaspoons sugar

3 teaspoons active dry yeast (from two 1/4-oz packages)

3 1/4 cups all-purpose flour plus additional for dusting

2 whole large eggs

1 large egg yolk

1 teaspoon pure vanilla extract

3/4 teaspoon salt

1 1/4 sticks (10 tablespoons) unsalted butter, cut into pieces and softened

1 tablespoon heavy cream or whole milk

5 tablespoons unsalted butter, well softened

2 (3 1/2- to 4-oz) bars fine-quality bittersweet chocolate (no more than 60% cacao if marked), finely chopped

1/4 cup sugar

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