反应详情

1-(4-Bromo-2-chloro-phenyl)-ethanone (from step 2 below) (1.86 g, 5.66 mmol), below was dissolved in ethylene glycol (5 mL). Triethylorthoformate (0.71 g, 4.79 mmol), and tosic acid (0.02 g) were added and reaction was stirred under nitrogen for 24 hours at room temperature. The resulting reaction mixture was poured into NaHCO3 (10 mL) and extracted with EtOAC. The combined organics were washed with water (10 mL) and brine (10 mL) then dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (5% EtOAc in Hexanes) to yield the intermediate ether as a colorless oil (0.69 g, 58%). 1H NMR (CDCl3): δ 1.77 (s, 3H), 3.74–3.79 (m, 2H), 4.04–4.09 (m, 2H), 7.37 (dd, J=8.5, 1.9 Hz, 1H), 7.52 (d, J=8.5 Hz, 1H), 7.55 (d, J=1.9 Hz, 1H). ESIMS (MH+): 278.2.

1. customreaction
2. customThe resulting reaction mixture
3. extractionextracted with EtOAC
4. washThe combined organics were washed with water (10 mL) and brine (10 mL)
5. dry with materialthen dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude residue was purified by flash chromatography (5% EtOAc in Hexanes)
9. customto yield the intermediate ether as a colorless oil (0.69 g, 58%)