Synthesis
General procedure for the synthesis of 1-bromo-2-iodo-4-methoxybenzene from 3-iodoanisole:
1. dissolve 3-iodoanisole (10.01 g, 42.77 mmol) in glacial acetic acid (65 mL).
2. 1-bromo-2-iodo-4-methoxybenzene bromide (2.8 mL, 54.49 mmol) was added dropwise to the above solution over 5 minutes.
3. The reaction mixture was stirred at room temperature for 24 hours to obtain an orange solution.
4. The reaction mixture was diluted with water and extracted with hexane.
5. The organic phases were combined and washed sequentially with 5% aqueous sodium thiosulfate and brine. 6.
6. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to give 1-bromo-2-iodo-4-methoxybenzene (13.51 g, quantitative yield). 7. The product was analyzed by 1H NMR.
7. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.47 (d, 1H), 7.39 (d, 1H), 6.77 (dd, 1H), 3.77 (s, 3H).
References
[1] Patent: WO2010/132016, 2010, A1. Location in patent: Page/Page column 127-128
[2] Chemistry - A European Journal, 2006, vol. 12, # 28, p. 7398 - 7410
[3] Organic Letters, 2011, vol. 13, # 10, p. 2614 - 2617
[4] Journal of Materials Chemistry C, 2016, vol. 4, # 25, p. 5981 - 5987
[5] Angewandte Chemie - International Edition, 2007, vol. 46, # 25, p. 4744 - 4747
