反应详情

温度

85 °C

To a well-stirred solution of ethyl 4-bromo-1-(5-chloro-2-nitrobenzyl)-1H-pyrrole-2-carboxylate (9.1 g, 23.48 mmoles) in acetic acid (60.00 mL) at 70° C., add iron (5 equiv; 6.56 g, 117.38 mmoles) in portions over 0.5 h. Halfway through the addition, observe an exotherm to maintain a temperature of 85° C. with the oil-bath removed. The reaction mixture will get thicker as the exotherm dissipates and the rest of the iron can be added. Stir at 85° C. for 0.5 h. Cool to room temperature and pour onto water (200 mL). Extract into chloroform (2×200 mL). Combine organic layers and wash with water (2×100 mL) then saturated aqueous NaHCO3 solution. Dry over Na2SO4, filter and evaporate to the title compound as an orange oil (7.7 g, 92% yield). MS (m/z): 358.98 (M+1).

1. additionHalfway through the addition
2. customremoved
3. customThe reaction mixture will get thicker as the exotherm dissipates
4. temperatureCool to room temperature
5. additionpour onto water (200 mL)
6. extractionExtract into chloroform (2×200 mL)
7. washCombine organic layers and wash with water (2×100 mL)
8. dry with materialDry over Na2SO4
9. filtrationfilter