Water → HCID 18782478, compound

Temperature

0 °C

Sodium hydride (60% dispersion in mineral oil, 870 mg, 21.7 mmol) was added to a stirred, cooled (0° C.) solution of N-[3-Bromo-4-(trifluoromethoxy)phenyl]trifluoroacetamide (Description 50, 6.3 g, 18.0 mmol) in DMF (50 ml). The mixture was stirred at 0° C. for 20 min. and methyl iodide (1.35 ml, 21.7 mmol) was added over 5 min. The mixture was stirred at 0° C. for 45 min. and at room temperature for 4 h. Water (100 ml) was added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic fractions were washed with water (3×100 ml) and brine (100 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 (3:1 increasing to 1:1) to give the title compound as a tan oil (1.20 g, 25%). 1H NMR (250 MHz, CDCl3) δ7.11 (1H, dq, J 8.9, 1.2 Hz), 6.86 (1H, d, J 2.8 Hz), 6.56 (1H, dd, J 8.9, 2.8 Hz), and 2.83 (3H, s).

1. stirringThe mixture was stirred at 0° C. for 45 min. and at room temperature for 4 h
2. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
3. washThe combined organic fractions were washed with water (3×100 ml) and brine (100 ml)
4. dry with materialdried (MgSO4)
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel
7. washeluting with hexane/CH2Cl2 (3:1 increasing to 1:1)

ORD record

ord-df97f5dcb9624a9a83fc6a37201b9bb3

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06071927