Methyl iodide → 2-Bromo-5-fluoroanisole

To a pre-cooled suspension of 2-bromo-5-fluorophenol (5 g, 26.18 mmol) and potassium carbonate (10.84 g, 78.54 mmol) in DMF (15 mL) at 0-5° C., was added methyl iodide (4.75 mL, 39.27 mmol) and the resulting reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (3×50 mL). The organic layers were combined, washed with saturated brine solution (20 mL) and dried over Na2SO4, filtered and concentrated in vacuo to afford 1-bromo-4-fluoro-2-methoxybenzene as a colourless liquid in 93% yield, 5.00 g.

1. customthe resulting reaction mixture
2. customThe reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL)
3. customThe organic layer was separated
4. extractionthe aqueous layer was further extracted with EtOAc (3×50 mL)
5. washwashed with saturated brine solution (20 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-97f07a49841b4a15b30b4fbd6be17c07

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952008B2