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ChemicalBook CAS DataBase List 2-Chlorobenzoxazole
615-18-9

2-Chlorobenzoxazole synthesis

7synthesis methods
2-Mercaptobenzoxazole

2382-96-9

2-Chlorobenzoxazole

615-18-9

General procedure for the synthesis of 2-chlorobenzoxazole from 2-mercaptobenzoxazole: 2-mercaptobenzoxazole (10 mmol, 1.51 g) was suspended in SOCl2 (50 mL), and a few drops of DMF were added as catalyst. The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the solvent was removed by evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/EtOAc, 10:1) to afford the target compound as a colorless oil in 69.7% yield.

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Yield:615-18-9 90%

Reaction Conditions:

with chlorine

Steps:

5 EXAMPLE 5
EXAMPLE 5 Example 1 is repeated, except that 2-chlorobenzoxazole is initially introduced, a temperature range of 20°-40° C. is used from the start, 830 g of 2-mercaptobenzoxazole are added and 586 g of chlorine are passed in. About 910 g of 2-chlorobenzoxazole are obtained after distillation under a water-jet vacuum at 107° C. Traces of ring-chlorinated product can be detected in the distillation residue. Yield: 90% of theory.

References:

Cassella Aktiengesellschaft US4517370, 1985, A

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