反应详情

温度

70 °C

A mixture of methyl 5-chloro-2-methyl-4-nitrobenzoate (862 mg, 4 mmol) and NBS (854 mg, 4.8 mmol) in MeCN (16 mL) was degassed and then AIBN (14 mg, 0.08 mmol) was added. The mixture was heated to 70° C. for 18 h. The solvent was removed in vacuo and the residue was partitioned between DCM (50 mL) and water (50 mL). The organic phase was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane) in order to remove baseline impurities gave methyl 2-(bromomethyl)-5-chloro-4-nitrobenzoate (1.09 g, 89%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 8.14 (s, 1H), 7.98 (s, 1H), 4.91 (s, 2H), 4.00 (s, 3H).

1. customwas degassed
2. customThe solvent was removed in vacuo
3. customthe residue was partitioned between DCM (50 mL) and water (50 mL)
4. customthe solvent was removed in vacuo
5. customPurification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane) in order
6. customto remove baseline impurities