Water → HCID 18782485, compound

Temperature

0 °C

Sodium hydride (60% dispersion in mineral oil, 0.48 g, 12 mmol) was added to a stirred, cooled (0° C.) solution of N-(3-Bromo-4-methoxyphenyl)trifluoroacetamide (Description 43, 2.98 g, 10 mmol) in dimethylformamide (30 ml). The mixture was stirred at 0° C. for 30 min., then methyl iodide (0.75 ml, 1.70 g, 12 mmol) was added. The mixture was stirred at 0° C. for 30 min., then at room temperature for 3 h. Water (50 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic fractions were washed with water (4×50 ml) and brine (50 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane/CH2Cl2 (50:50 increasing to 30:70) to give the title compound as a colorless solid (2.72 g, 87%). 1H NMR (250 MHz, CDCl3) δ7.46 (1H, d, J 2.4 Hz), 7.18 (1H, dd, J 8.7, 2.4 Hz), 6.91 (1H, d, J 8.7 Hz), 3.94 (3H, s), and 3.32 (3H, s).

1. stirringThe mixture was stirred at 0° C. for 30 min.
2. waitat room temperature for 3 h
3. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
4. washThe combined organic fractions were washed with water (4×50 ml) and brine (50 ml)
5. dry with materialdried (MgSO4)
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel
8. washeluting with hexane/CH2Cl2 (50:50 increasing to 30:70)

ORD record

ord-c011a1cf57444c3091b6cca9e209ae39

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06071927