反应详情

温度

100 °C

A solution of 4-methyl-2-chlorobenzonitrile (1.51 g, 10 mmol), N-bromosuccinimide (2.14 g, 12.0 mmol) and AIBN (33 mg, 0.20 mmol) in ACN (40 mL) was heated under reflux for 18 hours. The reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of Na2CO3 and brine. The organic layer was dried (MgSO4) and concentrated under vacuum. The residue was treated with sarcosine tert-butyl ester hydrochloride (1.44 g, 7.92 mmol) and K2CO3 (2.74 g, 19.8 mmol) in ACN (10 mL). The mixture was heated at 100° C. for 2 hours. The solvent was evaporated under vacuum. The residue was dissolved in a mixture of DCM and water and then poured through a hydrophobic frit. The solvent was evaporated under vacuum. The residue was purified by flash chromatography (silica, iso-hexane/Et2O) to afford the title compound (1.95 g, quantitative). 1H NMR (CDCl3, 400 MHz) δ 7.61 (1H, d, J=8.0 Hz), 7.57 (1H, s), 7.36 (1H, m), 3.73 (2H, s), 3.21 (2H, s), 2.36 (3H, s), 1.48 (9H, s).

1. temperatureunder reflux for 18 hours
2. washwashed with a saturated aqueous solution of Na2CO3 and brine
3. dry with materialThe organic layer was dried (MgSO4)
4. concentrationconcentrated under vacuum
5. customThe solvent was evaporated under vacuum
6. dissolutionThe residue was dissolved in a mixture of DCM and water
7. additionpoured through a hydrophobic frit
8. customThe solvent was evaporated under vacuum
9. customThe residue was purified by flash chromatography (silica, iso-hexane/Et2O)