Реакция #596404

Уравнение реакции

2,6-dimethylbromobenzene

diethyl malonate

P(tert-Bu)3

HBF4

K2CO3

→

ethyl 2,6-dimethylphenylacetate

Выход 81.0%

Условия реакции

Обработка

1. 1
   Другоеevacuated
2. 2
   workup.ADDITIONfilled with nitrogen
3. 3
   ТемператураAfter cooling to room temperature
4. 4
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate
5. 5
   ПромывкаThe resulting solution was washed successively with 20 ml each of water, saturated aq. NaHCO3 solution and saturated aqueous NaCl solution
6. 6
   Сушкаdried over MgSO4
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   ДругоеChromatographic purification

Методика

A dry Schlenk vessel was initially charged with 185 mg [1 mmol] of 2,6-dimethylbromobenzene, 1056 mg [6.6 mmol] of diethyl malonate, 2.88 mg [0.005 mmol] of Pd(dba)2, 3.19 mg [0.011 mmol] of P(tert-Bu)3×HBF4, 207 mg [1.5 mmol] of dried K2CO3 and 150 mg [1.5 mmol] of KHCO3. The reaction vessel was three times evacuated and filled with nitrogen. This was followed by stirring at 160° C. until completion of conversion (8 hours). After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. The resulting solution was washed successively with 20 ml each of water, saturated aq. NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated under reduced pressure. Chromatographic purification using silica gel (hexane/ethyl acetate) gave ethyl 2,6-dimethylphenylacetate in a yield of 81% of theory.

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