Hydroquinone → Fluazifop-butyl

참여 물질

반응 단계

Sodium (6.9 g, 0.3 mol) was added to n-butanol (200 ml) under nitrogen. When the sodium had reacted, the solution was cooled to room temperature and hydroquinone (16.5 g, 0.15 mol) was added. The temperature was raised to 45° and n-butyl 2-bromoacrylate (26 g, 0.125 mol) was added dropwise. When the acrylate had all been added, the mixture was stirred for 20 hours and then 2-chloro-5-trifluoromethylpyridine (27.2 g, 0.15 mol) was added. The resulting mixture was heated for 30 hours at 65°, allowed to cool, treated with carbon and filtered through Celite. The resulting solution was made up to 500 ml with n-butanol and a hydrogenation catalyst (10% palladium on carbon; 0.5 g) was added. The crude product was hydrogenated at ambient temperature and pressure until hydrogen uptake ceased to give n-butyl 2-[4-(5-trifluoromethylpyridin-2-yloxy)phenoxy]propionate.

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