5-Bromo-2-methylphenol

Light yellow solid

5-Bromo-2-methylphenol; A solution of concentrated sulphuric acid (6 mL) in distilled water (75 mL) was added to 5-bromo-2-methylaniline (1 g, 5.38 mmol). The resultant suspension was heated to 90° C. and stirred for 4.5 h. The reaction mixture was then cooled using an ice bath and a solution of sodium nitrite (384 mg, 5.57 mmol) in water (5 mL) was added to the reaction mixture at 0° C. The reaction was then allowed to warm to ambient temperature. The reaction mixture was then added to a solution of concentrated sulphuric acid (6 mL) in water (75 mL) which had been preheated to 90° C. The reaction mixture was stirred for 1 h at 90° C. and allowed to cool, on standing, overnight. A precipitate was observed in the reaction mixture. The precipitate was collected by filtration, washed with water, and dried in a vacuum oven to afford 5-bromo-2-methylphenol as a brown solid (510 mg, 2.73 mmol, 51percent). M.S. (ESI) (m/z) 185, 187[M-H]A solution of concentrated sulphuric acid (6ml_) in distilled water (75ml_) was added to 5- bromo-2-methylaniline (1g, 5.38mmol). The resultant suspension was heated to 9OTo a solution of 5-AMINO-2-METHYLPHENOL (10 G, 81.2 MMOL) in hydrobromic acid (40 mL, 48 percent solution) and water (50 mL) at 0 °C was added a solution of sodium nitrite (5.6 g, 81.2 MMOL) in water (15 mL) and the mixture stirred at this temperature for 30 minutes. To this was added copper (I) bromide (11.6 G, 81. 2 MMOL) in hydrobromic acid (15 mL, 48percent solution) and the reaction was subsequently heated at reflux for 2 hours. Upon cooling to room temperature the resulting mixture was extracted with ethyl acetate (2 x 200 mL) and the combined organic extracts were washed with aqueous potassium hydroxide solution (-1 M, 200 mL), dried (magnesium sulphate) and concentrated under reduced pressure. The crude product was purified by column chromatography [SI02 ; light petroleum to 4: 1 light petroleum-ethyl acetate] to give the title compound as a COLOURLESS OIL, WHICH CRYSTALLISED to give fine colourless needles upon standing overnight (4 G, 26 percent). Rf = 0.26 [4: 1 light petroleum-ethyl acetate]. 1H NMR 5 2.21 (3 H, s), 4.89-4. 95 (1 H, br, s), 6.96-6. 97 (1 H, br, m), 6.99-7. 00 (2 H, m).To a solution of 5-amino-2-methylphenol (50 g, 0.41 mol) in hydrobromic acid (200 mL, 48 percent solution) and water (200 ml) in a brine ice bath was added sodium nitrite (30.5 g, 0.45 mol, 1.1 equiv.) portion-wise at such a rate that the temperature remained below +10 Example 60; Synthesis of 4-(4-methyl-3-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide; Step 1; 5-Bromo-2-methylphenol; 5-Amino-2-methylphenol (5 g, 0.04 mol) was dissolved in HBr (20 mL) and H

Molecular Weight:187.03
XLogP3:2.7
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