Ingredients

1 1/4 cups water

15 ounces whole Medjool dates (about 22), pitted, plus 4 more, pitted and halved lengthwise, for garnish

3 tablespoons brandy

2 tablespoons strong-brewed coffee

4 tablespoons unsweetened Dutch-process cocoa powder

2 cups all-purpose flour

1 teaspoon salt

Pinch of ground cinnamon

1 1/2 sticks (12 tablespoons) unsalted butter, room temperature, plus more for pan

3/4 cup packed dark-brown sugar

4 large eggs

1 1/2 teaspoons baking soda

5 ounces bittersweet chocolate (preferably at least 61 percent cacao), coarsely chopped

1/2 stick (4 tablespoons) unsalted butter

2/3 cup packed light-brown sugar

1/3 cup light corn syrup

1 tablespoon water

Pinch of salt

2 tablespoons heavy cream

4 ounces bittersweet chocolate (preferably at least 61 percent cacao), finely chopped

1 tablespoon plus 1 1/2 teaspoons brandy

Preparation

For the cake: Preheat oven to 350 degrees. Butter a 9-by-3-inch round cake pan. Line with parchment, and butter parchment.

Bring water to a boil in a saucepan. Meanwhile, combine dates, brandy, coffee, and 2 tablespoons cocoa in a heatproof bowl. Stir in boiling water. Let cool, stirring occasionally. Puree cooled date mixture in a food processor (you should have about 2 1/2 cups). Place 3/4 cup puree in a small bowl, and press plastic wrap directly on surface; reserve. Place remaining puree in a large bowl.

Whisk flour, salt, cinnamon, and remaining 2 tablespoons cocoa in a bowl.

Beat butter and dark-brown sugar with a mixer on medium speed until fluffy. Add eggs, one at a time, beating after each addition (batter will look curdled).

Stir baking soda into reserved uncovered date puree. On low speed, beat flour mixture into egg mixture in 2 additions, alternating with the date mixture. Beat in chocolate. Transfer batter to prepared pan, and smooth top.

Bake until a toothpick inserted into center of cake comes out clean, about 1 hour. Let cool in pan on a wire rack for 30 minutes. Run a knife around edge of pan to loosen, and invert cake onto rack. Remove parchment, turn cake right side up, and let cool completely.

Make the glaze: Bring butter, light-brown sugar, corn syrup, water, and salt to a boil in a saucepan over medium-low heat, stirring occasionally. Boil 3 minutes. Remove from heat. Whisk in cream. Add chocolate, and whisk until smooth. Whisk in brandy. Let cool until thickened, 15 to 20 minutes.

Assemble the cake: Using a serrated knife, trim rounded top of cake so it is flat. Place cake on stand. Spread remaining 3/4 cup date puree over top of cake. Pour glaze over top, letting some drip down sides. Garnish with halved dates.