General procedure for the synthesis of 3-bromo-2-methylanisole from 3-bromo-2-methylphenol and iodomethane:
1. 3-Bromo-2-methylphenol (500 mg, 2.67 mmol) and potassium carbonate (1108 mg, 8.02 mmol) were added to dry DMF (10 mL) and stirred for 5 minutes at room temperature.
2. To the above mixture, iodomethane (0.836 mL, 13.37 mmol) was slowly added, and the reaction system was subsequently warmed up to 50 °C with continuous stirring for 2 hours.
3. After completion of the reaction, the mixture was poured into water (30 mL) and extracted with ethyl acetate (20 mL + 3 x 20 mL).
4. The organic phases were combined and concentrated under reduced pressure to afford the target product 3-bromo-2-methylanisole (450 mg, 80% yield). 5. The product was analyzed by LC-MS.
5. The product was analyzed by LC-MS and showed m/z 305.9 (M + H)+ with a retention time of 1.09 min.
[1] Synlett, 2009, # 15, p. 2483 - 2486
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 11040 - 11044
[3] Angew. Chem., 2018, vol. 130, # 34, p. 11206 - 11210,5
[4] Chemical Communications, 2003, # 10, p. 1170 - 1171
[5] Patent: WO2015/92713, 2015, A1. Location in patent: Page/Page column 201
