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ChemicalBook CAS DataBase List 6-CHLORO-2-(1,1-DIMETHYLETHYL)-7-BENZOXAZOLETHIOL

6-CHLORO-2-(1,1-DIMETHYLETHYL)-7-BENZOXAZOLETHIOL synthesis

4synthesis methods
-

Yield:954127-39-0 96%

Reaction Conditions:

Stage #1: 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloridewith triphenylphosphine in toluene; for 0.666667 h;Inert atmosphere;
Stage #2: with water in toluene; for 1 h;

Steps:

1 2-tert-Butyl-6-chlorobenzoxazole-7-thiol

10198] To a solution of 2-tert-butyl-6-chiorobenzoxazole-7-sulfonyl chloride (15.01 g; 48.70 mmol) under nitrogen in toluene (250 ml) is added a solution of triphenylphosphine (38.32 g; 146.11 mmol) in toluene (125 ml) (the reaction is exothermic). Afier 40 minutes, the reaction medium is hydrolysed with water (250 ml) and left stirring for 1 hour. The organic phase is then extracted twice with iN sodium hydroxide solution (2x125 ml). The basic aqueous phases are combined and washed twice with toluene (2x125 ml). The aqueous phase is then acidified to pH=1 with aqueous 2N hydrochloric acid solution and is then extracted twice with dichloromethane (2x1 50 ml). The organic phases are combined, dried over anhydrous sodium sulfate, filtered and concentrated. 2-tert-Butyl-6-chlorobenzoxazole-7-thiol (ii. 37 g; 96%) is obtained. MS (ES+) mlz 342/344 (MH+).

References:

US2017/349575,2017,A1 Location in patent:Paragraph 0198