Ethyl Acetate → 5-(2-(2-(2-(2-Bromoethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)-2-nitrobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-hydroxy-4-(2-methoxyethoxy)-2-nitrobenzonitrile (0.4 g) in DMF (8 mL) was added 1-bromo-2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethane (1.0 g) and K2CO3 (0.5 g). The resulting mixture was heated at 80° C. overnight under N2 atmospheres. After reaction finished, the mixture was diluted with water (50 mL) and exacted with EA (3×50 mL). The combined organic layer was dried over Na2SO4, concentrated under reduced pressure, and purification by silica chromatography to give 0.2 g of 5-(2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)-2-nitrobenzonitrile. 1H-NMR (400 MHz, CDCl3): δ: 7.85 (s, 1H), 7.33 (s, 1H), 4.33-4.28 (m, 4H), 3.95-3.92 (m, 2H), 3.83-3.79 (m, 4H), 3.74-3.72 (m, 2H), 3.69-3.66 (m, 6H), 3.49-3.47 (m, 2H), 3.45 (s, 3H).

Provenance & Evidence