343269-52-3

20294-50-2

343269-52-3

The general procedure for the synthesis of 2-amino-4-bromo-6-methylphenol from 4-bromo-2-methyl-6-nitrophenol was as follows: a concentrated hydrochloric acid solution of tin(II) chloride (5.31 g, 28.00 mmol) was prepared. Intermediate 34A (1.30 g, 5.60 mmol) was dissolved in methanol (25 mL) at 0 °C and hydrochloric acid (6.00 mL, 19.7 mmol) was added. The reaction mixture was stirred at room temperature for 14 h. The mixture was subsequently concentrated under reduced pressure and diluted with deionized water (100 mL). The mixture was alkalized with saturated sodium bicarbonate solution, filtered through diatomaceous earth (Celite) and the filtrate was extracted with dichloromethane (2 x 75 mL). The organic extracts were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give Intermediate 34B (0.90 g, 80.0% yield) as a brown solid.1H NMR (300 MHz, DMSO-d6) δ ppm 2.15 (s, 3H), 4.83 (br.s, 2H), 6.44 (d, J = 2.64 Hz, 1H), 6.61 (d, J = 2.27 Hz, 1H), 8.06 (br.s, 1H).LCMS (Method-D): retention time 2.93 min, [M + 2] 204.0.