BrBr.[Cl:3][C:4]1[CH:5]=[C:6]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:7](C(N)C#N)=[O:8].[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].Br.C([N:25](CC)[CH2:26][CH3:27])C.C([N:32](CC)CC)C>C(OCC)(=O)C.O.O1CCCC1>[CH2:17]([O:21][CH:27]([NH:32][C:7](=[O:8])[C:6]1[CH:13]=[C:14]([Cl:16])[CH:15]=[C:4]([Cl:3])[CH:5]=1)[C:26]#[N:25])[C:18]#[C:19][CH3:20]
Bromine (2.8 g) was added at a time to a solution of 4.0 g of 3,5-dichlorobenzoyl aminoacetonitrile in 100 ml of ethyl acetate at room temperature. The mixture was stirred until the color of bromine in the reaction solution disappeared. The reaction solution was then cooled to 0° to 5° C. A mixture of 1.5 g of 2-butyn-1-ol, 3.5 g of triethylamine and 30 ml of tetrahydrofuran was cooled to 0° to 5° C. on an ice bath, and with stirring, the ethyl acetate solution of the bromine compound prepared above was added dropwise. After the addition, the reaction was continued for 30 minutes under cooling. Water (100 ml) was added to dissolve the precipitated triethylamine hydrobromide. The oil layer was separated, washed with water, and dried. The solvent was then distilled off under reduced pressure. The residual solid was suspended in ethyl ether, filtered, washed and dried to give 4.2 g of the desired alpha-(2-butynyloxy)-3,5-dichlorobenzoylaminoacetonitrile as a white solid. The yield was 79.9%, and the melting point of the product was 124° to 128° C.
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