| 80% |
Stage #1: 2-fluoro-4-methyl-5-nitroaniline With hydrogenchloride In lithium hydroxide monohydrate at 0℃;
Stage #2: With NaNO2 In lithium hydroxide monohydrate at -10℃; for 0.666667h;
Stage #3: With potassium iodide In lithium hydroxide monohydrate at 0 - 20℃; for 2h; |
3 1-fluoro-2-iodo-5-methyl-4-nitrobenzene (11)
Aniline 10 (10.21 g, 60.00 mmol) was suspended in 36% m/m aqueous HC1 (120 mL) and the mixture cooled to <0 °C. To this mixture was added a solution of NaNC>2 (4.55 g, 66.00 mmol) in water (24 mL) dropwise over 10 minutes, maintaining the internal temperature at <0 °C, and the resulting mixture was stirred for 30 minutes at -10 °C. This diazonium salt solution was then added portionwise over 20 minutes to a solution of KI (19.92 g, 120 mmol) in water (36 mL) at 0 °C, making sure to maintain the internal temperature of the KI solution below 10 °C during the addition. The resulting very dark-brown mixture was then allowed to warm to room temperature and stirred for 2 h. To the reaction mixture was then added water (300 mL) , saturated aqueous a2S203 (50 mL) , and Et20 (200 mL) , and the mixture was shaken until the dark color was dissipated. The organic layer was separated and the remaining aqueous extracted with additional Et20 (2 x 200 mL) . The combined organics were washed with water (100 mL) and brine (100 mL) , dried over Na2SC , and concentrated to give a dark-orange oil mixed with yellow solids (15.85 g) . This material was purified by column chromatography (hexanes, 2 column volumes → 25:1 hexanes : Et20, 3 column volumes) to give the pure product 11 as a crystalline, pale- yellow solid (13.53 g, 80%) . *H NMR (400 MHz, CDCI3) δ 8.42 (d, J = 5.8 Hz, 1H), 7.03 (dd, J = 8.0, 0.8 Hz, 1H) , 2.59 (s, 3H) ; 13C NMR (101 MHz, CDCI3) δ 165.3 and 162.7, 145.8, 137.5 and 137.4, 136.4 and 136.3, 119.4 and 119.1, 77.8 and 77.5, 20.9. |
| 80% |
Stage #1: 2-fluoro-4-methyl-5-nitroaniline With hydrogenchloride; NaNO2 In lithium hydroxide monohydrate at -10℃; for 0.666667h; Inert atmosphere;
Stage #2: With potassium iodide In lithium hydroxide monohydrate at 0 - 20℃; for 2.33333h; Inert atmosphere; |
3.6 1-fluoro-2-iodo-5-xnethyl-4-nitrobenzene (11).
Aniline 10 (10.21 g, 60.00 mmol) was suspended in 36% m/m aqueous HC1 (120 mL) and the mixture cooled to (4.55 g, 66.00 mmol) iinn wwaatteerr (24 mL) dropwise over 10 minutes, maintaining the internal temperature aatt KI (19.92 9, 120 mmol) in water ((3366 mmLL)) at 0 °C, making sure to maintain the internal temperature of the KI solution below 10 °C during the addition. The resulting very dark-brown mixture was then allowed to warm to room temperature and stirred for 2 h. To the reaction mixture was then added water (300 mL), saturated aqueousNazSzOa (50 mL), and EtzO (200 mL), and the mixture was shaken until the dark color was dissipated. The organic layer was separated and the remaining aqueous extracted with additional EtzO (2 x 200 mL). The combined organics were washed with water (100 mL) and brine (100 mL), dried over NazSO4, and concentrated to give a dark-orange oil mixed with yellow solids (15.85 g). This material was purified by column chromatography (hexanes, 2 column volumes 25:1 hexanes:EtzO, 3 column volumes) to give the pure product 11 as a crystalline, paleyellow solid (13.53 g, 80%). 1H NMR (400 MHz, CDCI3) 5 8.42 (d, J =5.8 Hz, 1H), 7.03 (dd, J = 8.0, 0.8 Hz, 1H), 2.59 (s, 3H); 13C NMR(101 MHz, CDClg) 6165.3 and 162.7, 145.8, 137.5 and 137.4, 136.4 and136.3, 119.4 and 119.1, 77.8 and 77.5, 20.9. |
| 80% |
Stage #1: 2-fluoro-4-methyl-5-nitroaniline With hydrogenchloride; NaNO2 In lithium hydroxide monohydrate at -10℃; for 0.666667h; Inert atmosphere;
Stage #2: With potassium iodide In lithium hydroxide monohydrate at 0 - 20℃; for 2.33333h; Inert atmosphere; |
3.6 1-fluoro-2-iodo-5-xnethyl-4-nitrobenzene (11).
Aniline 10 (10.21 g, 60.00 mmol) was suspended in 36% m/m aqueous HC1 (120 mL) and the mixture cooled to (4.55 g, 66.00 mmol) iinn wwaatteerr (24 mL) dropwise over 10 minutes, maintaining the internal temperature aatt KI (19.92 9, 120 mmol) in water ((3366 mmLL)) at 0 °C, making sure to maintain the internal temperature of the KI solution below 10 °C during the addition. The resulting very dark-brown mixture was then allowed to warm to room temperature and stirred for 2 h. To the reaction mixture was then added water (300 mL), saturated aqueousNazSzOa (50 mL), and EtzO (200 mL), and the mixture was shaken until the dark color was dissipated. The organic layer was separated and the remaining aqueous extracted with additional EtzO (2 x 200 mL). The combined organics were washed with water (100 mL) and brine (100 mL), dried over NazSO4, and concentrated to give a dark-orange oil mixed with yellow solids (15.85 g). This material was purified by column chromatography (hexanes, 2 column volumes 25:1 hexanes:EtzO, 3 column volumes) to give the pure product 11 as a crystalline, paleyellow solid (13.53 g, 80%). 1H NMR (400 MHz, CDCI3) 5 8.42 (d, J =5.8 Hz, 1H), 7.03 (dd, J = 8.0, 0.8 Hz, 1H), 2.59 (s, 3H); 13C NMR(101 MHz, CDClg) 6165.3 and 162.7, 145.8, 137.5 and 137.4, 136.4 and136.3, 119.4 and 119.1, 77.8 and 77.5, 20.9. |
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