N-bromobutanimide → 2-Iodo-4-bromo-5-methoxy-1-methoxymethoxybenzene

Temperature

23 °C

To a stirred solution of 2-iodo-5-methoxy-1-methoxymethoxybenzene (5.24 g, 17.8 mmol) in MeCN (55 mL) was added silica gel (1.32 g), 2,6-di-tert-butyl-4-hydroxytoluene (60 mg), and then N-bromosuccinimide (3.17 g, 17.8 mmol). The mixture was stirred at 23° C. for 1 hour and then filtered. The filtrate was concentrated in vacuo and the residue was dissolved in CH2Cl2 (100 mL). To this solution was added water (100 mL) and the resulting mixture was vigorously stirred for 5 min. The layers were then separated and the aq. phase was extracted with CH2Cl2 (2×100 mL). The combined organics were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash-column chromatography (SiO2, petroleum ether:Et2O 8:1) to provide 2-iodo-4-bromo-5-methoxy-1-methoxymethoxybenzene as a yellow oil (5.05 g, 76%).

1. filtrationfiltered
2. concentrationThe filtrate was concentrated in vacuo
3. dissolutionthe residue was dissolved in CH2Cl2 (100 mL)
4. additionTo this solution was added water (100 mL)
5. stirringthe resulting mixture was vigorously stirred for 5 min
6. customThe layers were then separated
7. extractionthe aq. phase was extracted with CH2Cl2 (2×100 mL)
8. dry with materialThe combined organics were dried over MgSO4
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash-column chromatography (SiO2, petroleum ether:Et2O 8:1)

ORD record

ord-222d9f26f30248bf9a9caa8d223146b7

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013203B2