p-Fluoronitrobenzene → HCID 14121576, compound

Participants

Reaction Steps

20.0 g of 2-benzoylaminoethanol are suspended in 60 ml of chlorobenzene. To the suspension are added 9.7 g of 50% strength sodium hydroxide solution and stirred in for some time until a homogeneous syrup has formed. 1.5 g of tetrabutylammonium bromide are then added, followed dropwise in the course of 15 minutes by 14.3 g of 4-nitrofluorobenzene, and the temperature rises to about 28°-30° C. The yellowish suspension is stirred at 30° for 3 hours and at 45° for a further 5 hours until the conversion of the nitrofluorobenzene is complete. Water is then added to the reaction mixture, the pH value is brought to 5 and the chlorobenzene is driven off in vacuo with water, leaving behind a slightly yellow suspension. After cooling down, it is filtered, and the filtercake is washed with water to give N-[2-(4-nitrophenoxy)-ethyl]-benzamide of Example 3: ##STR37##

Provenance & Evidence