Methyl iodide → 1-Bromo-2-methoxy-5-methyl-3-nitrobenzene

2-Bromo-4-methyl-6-nitro-phenol 11b (22.24 g, 95.9 mmol) was dissolved in 150 mL of acetone, followed by addition of potassium carbonate (15.9 g, 115 mmol) and iodomethane (13.7 mL, 220.6 mmol). The reaction mixture was heated to reflux overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with 100 mL of ethyl acetate and filtered. The mixture was concentrated under reduced pressure to obtain the title compound 1-bromo-2-methoxy-5-methyl-3-nitro-benzene 11c (23.1 g, yield 97.9%) as an orange solid.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux overnight
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionThe residue was diluted with 100 mL of ethyl acetate
6. filtrationfiltered
7. concentrationThe mixture was concentrated under reduced pressure

ORD record

ord-143aadf36a0342eeb5c2baaea9543ba4

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2