Ethyl Bromide → 1-Ethoxy-2,5-difluoro-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-difluoro-4-nitro-phenol (4.86 g, 28.2 mmol) in acetonitrile (50 mL), potassium carbonate (4.7 g, 34 mmol) and bromoethane (4.21 mL, 56.4 mmol) were added. After stirring at 70° C. for 3.5 hours, iodoethane (2.73, 33.8 mmol) was added and mixture was stirred at 80° C. After 20 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-ethoxy-2,5-difluoro-4-nitro-benzene as a yellow solid (5.05 g, 88%). 1HNMR (CDCl3, 400 MHz) δ 7.92-7.88 (m, 1H), 6.82-6.78 (m, 1H), 4.21-4.16 (q, 1H), 4.13-4.07 (q, J=7.0 Hz, 2H), 1.54-1.51 (t, J=7.0 Hz, 3H).

Provenance & Evidence