Реакция #2028869

Уравнение реакции

HCl

Ethyl difluoroacetate

sodium methoxide

methanol

4′-chloroacetophenone

→

yellow solid

Выход 99.5%

4,4-difluoro-1-[4-(chloro)phenyl]-butane-1,3-dione

Выход 99.5%

Растворители

ether

diethyl ether

diethyl ether

Условия реакции

Обработка

1. 1
   workup.ADDITIONadded to the reaction dropwise over 5 minutes
2. 2
   workup.ADDITIONwere added
3. 3
   ДругоеThe organic layer was collected
4. 4
   Промывкаwashed with brine (250 mL)
5. 5
   Сушкаdried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated in vacuo

Методика

Ethyl difluoroacetate (24.82 g, 200 mmol) was placed in a 500 mL three-necked round bottom flash, and dissolved in diethyl ether (200 mL). To the stirred solution was added 25% sodium methoxide in methanol (48 mL, 210 mmol) via an addition funnel over a 2 minute period. Next, 4′-chloroacetophenone (25.94 g, 200 mmol) was dissolved in diethyl ether (50 mL), and added to the reaction dropwise over 5 minutes. After stirring overnight (18 hours), 1N HCl (250 mL) and ether (250 mL) were added. The organic layer was collected, washed with brine (250 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 46.3 g of a yellow solid. The solid was recrystallized from methylene chloride and iso-octane to give 31.96 g (69%) of the dione: mp 65°-66.5° C.

Источник