Heat oil and vanilla bean in a small saucepan until bean begins to bubble. Remove from heat; let stand 10 minutes or until mixture reaches room temperature. Scrape seeds from vanilla bean; add to oil. Discard bean.
Place brown sugar, butter, and vanilla oil in a large bowl; beat with a mixer at medium speed until well blended (about 5 minutes). Add eggs, 1 at a time, beating well after each addition.
Weigh or lightly spoon flour into dry measuring cups; level with a knife. Combine flour, baking powder, and salt, stirring with a whisk. Beating at low speed, add flour mixture and milk alternately to sugar mixture; beat until blended. Pour mixture into a 10-cup Bundt pan coated with baking spray. Bake at 350°F for 48 minutes or until a wooden pick inserted in center comes out clean. Cool in pan on a wire rack 10 minutes; remove cake from pan. Invert onto wire rack.
While cake bakes, bring granulated sugar and bourbon to a simmer in a small saucepan; cook 2 minutes or until sugar dissolves, stirring occasionally. Cool slightly. Brush bourbon mixture over warm cake until all is absorbed. Cool cake completely.
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