* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With tetra-n-butylammonium tribromide; In hexane; dichloromethane; ethyl acetate;
g. 2-bromo-5-methoxy-4-methyl-aniline. To a solution of 3-methoxy-4-methyl-aniline (8.19 g, 59.71 mmol) in dichloromethane (200 mL), was added tetrabutylammonium tribromide (28.79 g, 59.71 mmol) and the reaction mixture was stirred at room temperature for 2.5 hrs. Aqueous NaHCO3 was added and the layers separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 11.05 g of 2-bromo-5-methoxy-4-methyl-aniline (85% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.75 (s, 3 H), 3.95 (br s, 1 H), 6.27 (s, 1 H), 7.13 (s, 1 H).
With tetra-N-butylammonium tribromide; In chloroform; at 0℃; for 0.333333h;
Reference Production Example 79 (1473) A mixture of 6.85 g of 3-methoxy-4-methylaniline and 150 mL of chloroform was cooled to 0 C. and 26.5 g of tetrabutylammonium tribromide was added, followed by stirring at the same temperature for 20 minutes. To the reaction mixture, chloroform was added. The organic layer was washed with a sodium bicarbonate solution, an aqueous sodium sulfite solution, water, and a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. (1474) The residue thus obtained was subjected to silica gel column chromatography to obtain 7.85 g of 2-bromo-5-methoxy-3-methylalanine. (1475) 1H-NMR (CDCl3) delta: 2.08 (3H, s), 3.76 (3H, s), 3.93 (2H, br s), 6.28 (1H, s), 7.12 (1H, s).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
