Benzene, 1,4-difluoro-2-nitro-5-propoxy- synthesis

Yield: 47%

Reaction Conditions:

with potassium carbonate in acetonitrile at 60; for 15 h;

Steps:

9.1.C
To a solution of 2,5-difluoro-4-nitro-phenol (1.71 g, 9.77 mmol) in acetonitrile (20 mL), potassium carbonate (2.7 g, 19.5 mmol) and 1-iodopropane (1.14 mL, 11.7 mmol) were added. After stirring at 60° C. for 15 hours, mixture was concentrated and extracted with methylene chloride and 2M NaOH solution. Organic phases were dried over magnesium sulfate, filtered, and concentrated to give 1,4-difluoro-2-nitro-5-propoxy-benzene as a yellow solid (0.995 g, 47%). ¹HNMR (CDCl₃, 400 MHz) δ 7.92-7.88 (m, 1H), 6.83-6.78 (m, 1H), 4.08-4.05 (t, J=6.5 Hz, 2H), 1.95-1.86 (m, 2H), 1.10-1.06 (t, J=7.4 Hz, 2H).

References:

Jones, Robert M.;Lehmann, Juerg;Wong, Amy Siu-Ting;Hurst, David;Shin, Young-Jun US2006/155128, 2006, A1 Location in patent:Page/Page column 48