Hexane → HCID 69205124, compound

To a solution of 4-bromo-2-ethoxy-1-methoxy-benzene (0.67 g, 2.9 mmol) in THF (10 mL) was added a solution of n-butyllitium in hexane (1.1 mL, 2.5 N, 2.8 mmol) at −78° C. and kept for 20 min. To the mixture was added a solution of 3-fluoro-4,N-dimethoxy-N-methyl-benzamide (0.56 g, 2.6 mmol) in THF (4 mL) at −78° C. After 2 h, isopropanol (1 mL) and water (30 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL) and dried over magnesium sulfate. Removal of solvent and chromatography (Silica Gel) gave (3-ethoxy-4-methoxy-phenyl) -(3-fluoro-4-methoxy-phenyl)-methanone (350 mg, 44% yield): 1H NMR (DMSO-d6) δ 1.49 (t, J=7 Hz, 3H, 2CH3), 3.96 (s, 3H, CH3), 3.98 (s, 3H, CH3), 4.16 (q, J=7 Hz, 2H, CH2), 6.90 (d, J=8 Hz, 1H, Ar), 7.02 (t, J=9 Hz, 1H, Ar), 7.35 (dd, J=2, 8 Hz, 1H, Ar), 7.41 (d, J=2 Hz, 1H, Ar), 7.55-7.62 (m, 2H, Ar).

1. waitAfter 2 h
2. customthe cold bath was removed
3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
4. washThe combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL)
5. dry with materialdried over magnesium sulfate
6. customRemoval of solvent and chromatography (Silica Gel)

ORD record

ord-6c056e3b4e5746e6868975e23f2c2418

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2