Reaktion #964356

Reaktionsgleichung

methyl 2-bromo-2-methylpropanoate

sodium bicarbonate

methyl 2-bromo-2-methylpropanoate

cesium carbonate

methyl 2-bromo-2-methylpropanoate

2-methyl-3-nitrophenol

→

Methyl 2-methyl-2-(2-methyl-3-nitrophenoxy)propanoate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at 100° C. for another 1 d
2. 2
   workup.STIRRINGthe mixture was stirred at 100° C. for another 1 d
3. 3
   TemperaturAfter cooling
4. 4
   Extraktionthe mixture was extracted repeatedly with ethyl acetate
5. 5
   WaschenThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution
6. 6
   Trocknendried over sodium sulfate
7. 7
   Einengenconcentrated on a rotary evaporator
8. 8
   SonstigeThe residue was purified by preparative HPLC

Vorschrift

2.00 g (13.06 mmol) of 2-methyl-3-nitrophenol were dissolved in 40 ml of DMF, and 3.55 g (19.59 mmol) of methyl 2-bromo-2-methylpropanoate and 4.68 g (14.37 mmol) of cesium carbonate were added. The reaction mixture was stirred at 100° C. for 2 d, and a further 1.77 g (9.80 mmol) of methyl 2-bromo-2-methylpropanoate were then added. The mixture was stirred at 100° C. for another 1 d, a further 1.77 g (9.80 mmol) of methyl 2-bromo-2-methylpropanoate were then added and the mixture was stirred at 100° C. for another 1 d. After cooling, saturated aqueous sodium bicarbonate solution was added and the mixture was extracted repeatedly with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated on a rotary evaporator. The residue was purified by preparative HPLC. This gave 1.33 g (39% of theory) of the target compound.

Quelle