Methyl iodide → 1-Bromo-2-fluoro-4-methoxybenzene

Temperature

30 °C

Into a 250-mL round-bottom flask, was placed 4-bromo-3-fluorophenol (5.0 g, 26.18 mmol, 1.00 equiv), tetrahydrofuran (50 mL). This was followed by the addition of potassium hydroxide (2.94 g, 52.40 mmol, 2.00 equiv) in portions. To this was added CH3I (5.6 g, 39.45 mmol, 1.51 equiv) dropwise. The resulting solution was stirred for 4 h at 30° C. TLC (Petroleum ether: EtOAc=1:4) controlled the reaction process. The reaction was then quenched by the addition of 30 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with petroleum ether. This resulted in 5.2 g (97%) of 1-bromo-2-fluoro-4-methoxybenzene as yellow oil.

1. customInto a 250-mL round-bottom flask, was placed
2. customThe reaction was then quenched by the addition of 30 mL of water
3. extractionThe resulting solution was extracted with 3×30 mL of ethyl acetate
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under vacuum
6. customThis resulted in 5.2 g (97%) of 1-bromo-2-fluoro-4-methoxybenzene as yellow oil

ORD record

ord-b72436c2b6344850b65a066f5bcbdd6a

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1