Iodine → Benzoic acid, 4-fluoro-2-methyl-, ethyl ester

Temperatur

-78 °C

Magnesium (0.644 g, 26.5 mmol) was added wit THF (4 mL) and a small amount of iodine. After the mixture was stirred, the mixture was added dropwise with a solution of 1-bromo-4-fluoro-2-methylbenzene (5.00 g, 26.5 mmol) in THF (50 mL). The mixture was stirred at room temperature for 30 minutes, and then cooled at −78° C. and added dropwise with a solution of ethyl chloroformate (3.80 mL, 39.8mmol) in THF (40 mL). The mixture was warmed slowly up to room temperature and stirring was continued at room temperature for 2 hours. The reaction mixture was diluted with ether and washed with water, saturated aqueous sodium bicarbonate solution, and then with saturated brine, and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated, and the resulting oily substance was purified by silica gel column chromatography (hexane/ether) to obtain the title compound (3.65 g, yield: 76%).

1. stirringThe mixture was stirred at room temperature for 30 minutes
2. temperatureThe mixture was warmed slowly up to room temperature
3. stirringstirring
4. washwashed with water, saturated aqueous sodium bicarbonate solution
5. dry with materialwith saturated brine, and dried over sodium sulfate
6. customThe drying agent was removed by filtration
7. concentrationthe filtrate was concentrated
8. customthe resulting oily substance was purified by silica gel column chromatography (hexane/ether)

ORD-Eintrag

ord-b39cfcc906414e23a88dea1133e7363f

Quelldatensatz

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07166617B2