627527-23-5

light yellow liquid

1. 3-Methoxy-5-trifluoromethylaniline (20 g, 104.6 mmol) was added batchwise to a cooled solution of sodium nitrite (7.392 g, 107.1 mmol) in sulfuric acid (74 ml) and acetic acid (88 ml). 2. The mixture was added dropwise to a vigorously stirred solution of cuprous bromide (18 g, 62.8 mmol) in 48% hydrobromic acid (200 ml) at 0°C. 3. The reaction mixture was stirred for 45 minutes at room temperature. 4. The reaction mixture was poured into ice water and the aqueous phase was extracted with dichloromethane. 5. The organic layer was separated. (200 ml) solution. 3. The reaction mixture was stirred at room temperature for 45 min. 4. The reaction mixture was poured into ice water and the aqueous phase was extracted with dichloromethane. 5. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and the solvent was evaporated at low temperature. 6. The residue was stirred in sodium bicarbonate solution and extracted with diisopropyl ether. 7. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and the solvent was evaporated to obtain intermediate 3-bromo-5-bromo-5-hydroxybromide. 8. The intermediate 3-bromo-5-trifluoromethyl anisole was obtained (12.7 g, 48% yield).

[1] Patent: WO2011/33018, 2011, A1. Location in patent: Page/Page column 38
[2] Patent: US2012/172354, 2012, A1. Location in patent: Page/Page column 17