Dimethylformamide → 1-Ethoxymethoxy-4-pentafluoroethyl benzene

Temperature

145 °C

A mixture of 7.5 g of the crude product of 1-ethoxymethoxy-4-iodobenzene, 10.0 g of sodium pentafluoropropionate, 10.27 g of copper(I) iodide, 120 ml of DMF and 45 ml of toluene was stirred at 140 to 150° C. for 1 hour to distill about 40 ml of toluene away. The reaction mixture was refluxed at 160 to 170° C. for further 5 hours, then cooled to room temperature, and added to ice water. To this mixture was added 200 ml of diethyl ether. This mixture was filtered through Celite (registered trademark), and the filtrate was extracted with diethyl ether. The combined organic layers were washed with water and saturated brine and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 5.45 g of 1-ethoxymethoxy-4-(pentafluoroethyl)benzene.

1. distillationto distill about 40 ml of toluene away
2. temperatureThe reaction mixture was refluxed at 160 to 170° C. for further 5 hours
3. temperaturecooled to room temperature
4. additionadded to ice water
5. additionTo this mixture was added 200 ml of diethyl ether
6. filtrationThis mixture was filtered through Celite (registered trademark)
7. extractionthe filtrate was extracted with diethyl ether
8. washThe combined organic layers were washed with water and saturated brine
9. dry with materialdried over magnesium sulfate
10. concentrationThe resulting mixture was concentrated under reduced pressure

ORD record

ord-65a4bff7c35b404e9c7383d8cf424c3b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796306B2