反应详情

温度

110 °C

Methyl 3-bromo-4-tert-butyl-benzoate (2.26 g, 4.17 mmol) was dissolved in dry DMF (2.1 mL) before CuCN (821 mg, 9.17 mmol) and NaCN (1.0 mg, 0.021 mmol) were added. The mixture was flushed with nitrogen and was stirred at 110° C. for 24 h. The reaction mixture was diluted with ethyl acetate (70 mL) and was washed with water. The organics were dried over sodium sulfate and were evaporated to dryness. The crude material was purified by column chromatography eluting with 0-10% ethyl acetate in hexanes to give methyl 4-tert-butyl-3-cyano-benzoate (390 mg, 43%). ESI-MS m/z calc. 217.1. found 218.5 (M+1)+; Retention time: 2.07 minutes (3 min run). NMR (400 MHz, CD3CN) δ 8.31 (d, J=1.8 Hz, 1H), 8.16 (dd, J=8.4, 2.0 Hz, 1H), 7.72 (d, J=8.4 Hz, 1H), 3.92 (s, 3H), 1.55 (s, 9H).

1. additionwere added
2. customThe mixture was flushed with nitrogen
3. additionThe reaction mixture was diluted with ethyl acetate (70 mL)
4. washwas washed with water
5. dry with materialThe organics were dried over sodium sulfate
6. customwere evaporated to dryness
7. customThe crude material was purified by column chromatography
8. washeluting with 0-10% ethyl acetate in hexanes