Water → Methyl 2-(3-bromo-4-methoxyphenyl)acetate

Methyl iodide (2.05 mL, 4.68 g, 33 mmol) was added to a mixture of methyl 3-bromo-4-hydroxyphenylethanoate (Description 73, 7.35 g, 30 mmol) and potassium carbonate (8.29 g, 60 mmol) in dimethylformamide (30 mL) and the mixture was stirred at room temperature for 16 h. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic fractions were washed with aqueous sodium hydroxide (1M, 2×100 mL), water (2×100 mL) and brine (100 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (7.65 g, 100%). 1H NMR (360 MHz, CDCl3) δ7.47 (1 H, d, J 2.1 Hz), 7.18 (1 H, dd, J 8.4, 2.1 Hz), 6.85 (1 H, d, J 8.4 Hz), 3.88 (3 H, s), 3.70 (3 H, s), and 3.49 (2 H, s).

1. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
2. washThe combined organic fractions were washed with aqueous sodium hydroxide (1M, 2×100 mL), water (2×100 mL) and brine (100 mL)
3. dry with materialdried (MgSO4)
4. customthe solvent was evaporated under reduced pressure

ORD record

ord-b96a4f206ec94080a4bb1c17563404f0

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06071927