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ChemicalBook CAS DataBase List 1-Methoxy-2,4-dinitrobenzene
119-27-7

1-Methoxy-2,4-dinitrobenzene synthesis

12synthesis methods
2,4-Dinitrochlorobenzene is treated with methanolic sodium hydroxide in a process similar to that described for 4-nitroanisole. 2,4-Dinitrophenetole [610-54-8] is similarly manufactured by using ethanol.
-

Yield:119-27-7 91%

Reaction Conditions:

with nitric acid;trifluoroacetic acid in water at 80; for 18 h;regioselective reaction;

Steps:

1-Methoxy-2,4-dinitrobenzene (7b)[3]
An round bottle flask was charged with a magnetic stir bar, arylboronic acid 7a (0.5 mmol), trifluroacetic acid 1.0 mL and 92.6 mg of 68% nitric acid aqueous solution (HNO3 1.0 mmol), then reacted at 80 °C under air atmosphere for 18h. The reaction was stopped and cooled to room temperature. The reaction mixture was directly passed through Celite and rinsed with an additional 30 mL of AcOEt. The combined filtrate was washed by 1 mol/L NaHCO3, H2O, then dried by NaSO4. The dried AcOEt solution was concentrated and purified by column chromatography to give the product 7b (90 mg, 91%) as white solid. Mp 93-96 °C; 1H NMR (400MHz, CDCl3/TMS): δ 4.10 (s, 3H), δ 7.22 (d, J = 8.8 Hz, 1H), δ 8.46 (dd, J1 = 9.2 Hz, J2 = 2.8 Hz, 1H), δ 8.76 (d, J = 2.8 Hz, 1H). 13C NMR (100MHz, CDCl3/TMS): 57.6, 113.8, 122.0, 129.3, 139.0, 140.3, 157.4. MS (EI) m/z (M+) 198.0.

References:

Shen, Guodong;Zhao, Lingyu;Liu, Wanxing;Huang, Xianqiang;Song, Huina;Zhang, Tongxin [Synthetic Communications,2017,vol. 47,# 1,p. 10 - 14] Location in patent:supporting information

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