| 80% |
|
EXAMPLE 100; A. Preparation of l-tert-Butyl-3-iodo-benzene from 3- (tert- Butyl) aniline; 3- (tert-Butyl) aniline (Oakwood, 6.0 g, 40.21mmol) was slowly added to a cold solution of 12 N HC1 (24. 5 mL) while stirring over an ice/acetone bath in a three-neck round bottom flask equipped with a thermometer. A 2.9M solution of sodium nitrite (16 mL) was added via addition funnel to the reaction flask at a rate so as maintain the temperature below 2°C. The solution was stirred for 30 min. prior to being added to a reaction flask containing a 4.2M solution of potassium iodide (100 mL). The reaction mixture was allowed to stir overnight while warming to RT. The mixture was then extracted with a hexane/ether solution (1: 1) followed by washing with H20 (2X), 0.2N citric acid (2X) and sat. NaCl. The organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (100percent Hexane) to give the desired iodo intermediate (8.33g, 80percent) |
| 80% |
|
3-(fert-Butyl) aniline (Oakwood, 6.0 g, 40.21 mmol) was slowly added to a cold solution of 12 N HCI (24. 5 mL) while stirring over an ice/acetone bath in a three-neck round bottom flask equipped with a thermometer. A 2.9 M solution of sodium nitrite (16 mL) was added via addition funnel to the reaction flask at a rate so as maintain the temperature below 2 C. The solution was stirred for 30 min prior to being added to a reaction flask containing a 4.2 M solution of potassium iodide (100 mL). The reaction mixture was allowed to stir overnight while warming to RT. The mixture was then extracted with a hexane/ether solution (1: 1) followed by washing with H20 (2X), 0.2N citric acid (2X) and sat. NaCl. The organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (100percent Hexane) to give the desired iodo intermediate (8. 33g, 80percent) : H NMR (CDCI3, 300 MHz) 8 1.34 (s, 9H), 7.07 (t, J = 8. 0 Hz, 1H), 7.39 (d, J = 8.0 Hz, 1H), 7.55 (d, J = 8.0 Hz, 1H), 7.77 (t, J = 2.0 Hz, 1 H). |
| 80% |
|
3- (tert-Butyl) aniline (Oakwood, 6.0 g, 40.21 mmol) was slowly added to a cold solution of 12 N HCI (24.5 mL) while stirring over an ice/acetone bath in a three-neck round bottom flask equipped with a thermometer. A 2.9 M solution of sodium nitrite (16 mL) was added via addition funnel to the reaction flask at a rate so as maintain the temperature below 2 °C. The solution was stirred for 30 min. prior to being added to a reaction flask containing a 4.2 M solution of potassium iodide (100 mL). The reaction mixture was allowed to stir overnight while warming to room temperature. The mixture was then extracted with a hexane/ether solution (1: 1) followed by washing with H20 (2X), 0.2 N citric acid (2X) and saturated NaCI. The organic phase was separated, dried (sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash chromatography (100percent Hexane) to give the desired iodo intermediate (8.33g, 80percent) : 1H NMR (CDCI3, 300 MHz) 8 1.34 (s, 9H), 7.07 (t, J = 8.0 Hz, 1 H), 7.39 (d, J = 8.0 Hz, 1H), 7.55 (d, J = 8.0 Hz, 1 H), 7.77 (t, J = 2.0 Hz, 1 H). |
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