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ChemicalBook CAS DataBase List 2-ETHOXY-4-FLUORO-1-NITROBENZENE

2-ETHOXY-4-FLUORO-1-NITROBENZENE synthesis

6synthesis methods
-

Yield:28987-44-2 100%

Reaction Conditions:

with potassium carbonate in acetone; for 15 h;Reflux;

Steps:

Intermediate 2: 2-Ethoxy-4-fluoro-1-nitrobenzene

Intermediate 2: 2-Ethoxy-4-fluoro-1-nitrobenzene
To a 100 mL round-bottomed flask were added a mixture of 5-fluoro-2-nitrophenol (3.14 g, 20.0 mmol), iodoethane (3.43 g, 22.0 mmol), K2CO3 (5.52 g, 40.0 mmol), and acetone (30.0 mL).
The mixture was heated at reflux for 15 h, and then concentrated under vacuum to dryness.
Water (30 mL) was added to the residue and the resulting mixture was extracted with EtOAc (3*20 mL).
The combined organic phases were washed with saturated NaCl(aq) (30 mL), dried over anhydrous Na2SO4, and concentrated to dryness to give the title compound (3.7 g, 100%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.92 (dd, J=9.0, 6.0 Hz, 1H), 6.80-6.65 (m, 2H), 4.17 (q, J=7.0 Hz, 2H), 1.51 (t, J=7.0 Hz, 3H).

References:

US2018/289706,2018,A1 Location in patent:Paragraph 0379; 0380