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Arrange a rack in the middle of the oven and heat to 400°F. Coat a 10-inch cast iron skillet with the butter and set aside.
Place the milk, sugar, eggs, and vanilla in a blender or food processor fitted with the blade attachment and process until the batter is smooth, about 20 seconds. Add the flour, cocoa powder, and salt and pulse until just incorporated, 5 to 7 pulses.
Arrange the pear slices in a single layer in the prepared pan, fanned out in a circle. Pour the batter evenly over the pears, then sprinkle the chopped chocolate on top.
Bake until the clafoutis is set, puffed, and light golden-brown around the edges, about 35 minutes. Place the skillet on a wire rack and let cool for 15 minutes. Cut into wedges or scoop and serve warm.