反应详情

A solution of m-tolyl-acetic acid methyl ester (11.41 g, 69.49 mmol), N-bromosuccinimide (12.59 g, 70.73 mmol), AIBN (100 mg) in CCl4 (200 mL) was heated at reflux for 16 h. The reaction was cooled to room temperature and aqueuos NaHCO3 (satd) was added. The aqueous solution was extracted with CH2Cl2 (2×) and the organic solution was dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (hexanes to 9:1 hexanes:EtOAc) provided the title compound as a clear and colorless liquid (11.99 g). 1H NMR (CDCl3 400 MHz) δ 7.27 (m, 4H), 4.47 (s, 2H), 3.69 (s, 3H), 3.62 (s, 2H).

1. temperatureat reflux for 16 h
2. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
3. dry with materialthe organic solution was dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customPurification by flash chromatography (hexanes to 9:1 hexanes:EtOAc)