Water → HCID 59295488, compound

Participants

Reaction Steps

To a solution of 2-Chloro-4-hydroxy-benzonitrile (1.6 g, 10.1 mmol) in dry dimethylformamide (30 mL) is carefully added sodium hydride (486 mg, 12.1 mmol). The resulting mixture is stirred for 20 minutes at room temperature. A solution of Methanesulfonic acid 2-bromo-4-methyl-thiazol-5-ylmethyl ester (3.0 g, 10.1 mmol) in dry dimethylformamide (5 mL) is added and the reaction mixture is stirred at room temperature. The reaction mixture is diluted with 100 mL of ethyl acetate after 5 h and water (20 mL) is carefully added (Caution: development of H2). The phases are separated and the organic phase is dried over MgSO4. The solvent is removed under reduced pressure and the crude product is purified by reversed phase HPLC to yield 2.2 g of 4-(2-Bromo-4-methyl-thiazol-5-ylmethoxy)-2-chloro-benzonitrile. C12H8BrClN2OS (343.63), MS (ESI): 343.0 (M+H+).

Provenance & Evidence