反应详情

Into a 500 mL flask was weighed 19.3 g (53 mmol) of 5-bromomethyl-1-(2,6-dichloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester, 13.7 g (79 mmol) of 4-bromophenol, 10.9 mg (79 mmol) of potassium carbonate, and 100 mL of ACN. The reaction mixture was heated to reflux for 4 h. After cooling, the crude reaction mixture was washed into a separatory funnel with ethyl acetate and water. The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with DCM-methanol (100:0 to 98:2) to afford 5-(4-bromophenoxymethyl)-1-(2,6-dichlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester as an off white solid (25.3 g, 100%); 1H NMR (400 MHz, CDCl3): δ 7.45 (m, 6H), 7.06 (s, 1H), 6.67 (d J=8.8 Hz 2H), 4.88 (s, 2H), 4.43 (q, J=7.07 Hz 2H), 1.41 (t, J=7.07 Hz 3H), MS (ES): 491 [M+Na]+.

1. customInto a 500 mL flask was weighed
2. temperatureThe reaction mixture was heated
3. temperatureto reflux for 4 h
4. temperatureAfter cooling
5. customthe crude reaction mixture
6. washwas washed into a separatory funnel with ethyl acetate and water
7. customThe organic layer was separated
8. washwashed with brine
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated in vacuo
11. customThe residue was purified by column chromatography on silica eluting with DCM-methanol (100:0 to 98:2)