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

2-Bromo-4-fluoro-6-nitro-phenol 2b (24.7 g, 104.7 mmol) and potassium carbonate (17.34 g, 125.6 mmol) were dissolved in 300 mL of acetone followed by addition of iodomethane (9.8 mL, 157.1 mmol). The reaction mixture was heated to reflux at 80° C. for 22 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and diluted with 200 mL of ethyl acetate and 200 mL of water. The aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic extracts were washed with 4 N hydrochloric acid and saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 1-bromo-5-fluoro-2-methoxy-3-nitro-benzene 2c (16.18 g, yield 61.8%) as a white solid.

1. temperatureThe reaction mixture was heated
2. concentrationThe mixture was concentrated under reduced pressure
3. additiondiluted with 200 mL of ethyl acetate and 200 mL of water
4. extractionThe aqueous layer was extracted with ethyl acetate (100 mL×2)
5. washThe combined organic extracts were washed with 4 N hydrochloric acid and saturated aqueous sodium bicarbonate
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography

ORD-Eintrag

ord-e793b0c4259b4c48a421cf4815d51cbe

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08367710B2