3-BROMO-2-METHYLPHENOL

68A.20 g (107 mmol) of 3-bromo-2-methylphenylamine are dissolved in 150 mL of aqueous 1.0M sulphuric acid and the mixture is cooled to 0° C. A solution of 8.9 g (129 mmol) of sodium nitrite in 20 mL of water is added slowly. 31 mL of 1N sulfuric acid aqueous solution was added to 3-bromo-2-methylaniline (4.04 g, 21.7 mmol), andthe mixture was cooled to 0°C. Sodium nitrite (6.0 M aqueous solution, 4.3 mL) was slowly added thereto. After 15minutes, 10 mL of sulfuric acid was added thereto, and the mixture was stirred for 1 hour under reflux. The reactionsolution was cooled to room temperature. After addition of water, the reaction solution was extracted with Et2O. Theorganic layer was dried with anhydrous magnesium sulfate and purified by column chromatography to obtain the titlecompound (2.34 g, 58 percent).1H-NMR (CDCl3) δ 7.14 (1H, d), 6.92 (1H, t), 6.71 (1H, d), 4.83 (1H, brs), 2.34 (3H, s)At -5°C 3-bromo-2-methylaniline is dissolved in 1 M sulfuric acid (20 mL). A solution of sodium nitrite (1 .4 g) in water (3 mL) is added dropwise and the mixture is stirred for 15 minutes. Then concentrated sulfuric acid (6.8 mL) is added dropwise and the mixture is heated for 1 hour to 100°C. The mixture is cooled to 0°C, diluted with water and extracted twice with diethylether. The combined organic phases are dried (MgSOTo a flask containing aqueous sulfuric acid (14percent, 260 mL), 3-bromo-2-methylaniline (5.00 mL, 40.6 mmol) was added. The mixture was brought to reflux, and a solution of sodium nitrite (3.08 g, 44.6 mmol) in water (minimum amount required to dissolve) was added dropwise over the course of 1 hour. The mixture was refluxed an additional 30 minutes, cooled to room temperature, and extracted three times with chloroform. The combined chloroform layeres were extracted three times with aqueous sodium hydroxide (1 M). The aqueous layers were acidified with concentrated hydrochloric acid and extracted three times with chloroform. These three chloroform extracts were combined, dried over magnesium sulfate, filtered, and concentrated to give 3-bromo-2-methylphenol (10-1, 5.63 g) as a brown solid.

Molecular Weight:187.03
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:185.96803
Monoisotopic Mass:185.96803
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes