C([O:4][C:5]([CH3:7])=[CH2:6])(=O)C.[Cl:8][C:9]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[C:10]=1N.C(=O)([O-])[O-].[K+].[K+].N(OC(C)(C)C)=O>CC(C)=O>[Cl:8][C:9]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[C:10]=1[CH2:4][C:5](=[O:6])[CH3:7]A mixture of isopropenyl acetate (12.2 g, 122 mmol), 2,4,6-trichloroaniline (16.0 g, 81.4 mmol), potassium carbonate (100 mg, 0.7 mmol), and acetone (100 g) was cooled to 10° C. tert-Butyl nitrite (90%, 10 g, 87.3 mmol) was dosed over 30 minutes. The reaction was stirred for further 90 minutes, and it was concentrated to a black oil. The residue was triturated with water, and the pH was adjusted to 10.5 with sodium hydroxide solution. The precipitate was filtered and recrystallized from methanol-water 1:1. The solid was filtered, washed with methanol-water 1:1, and dried. The product was obtained as dark-brown crystalline material (15.9 g, 70.7% purity, 47.3 mmol, 58% yield). Further purification was achieved by recrystallization from hexanes. 1H NMR (400 MHz, CDCl3): δ 2.23 (s, 3H, CH3), 4.02 (s, 2H, CH2), 7.31 (s, 2H, CH).
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