反应详情

温度

90 °C

A mixture of 4-bromomethylphthalic acid dimethyl ester (3.1 g, 10.8 mmol), 2-(tert-butoxycarbonylamino)phenylboronic acid (4.3 g, 18.1 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.6 g), 2 M aqueous sodium carbonate (20 ml), and 1,2-dimethoxyethane (40 ml) was heated at 90° C. for 19 hours. The reaction mixture was cooled to room temperature and partioned between water (60 ml) and methylene chloride (60 ml). The organic phase was isolated, washed with water (2×50 ml), dried over magnesium sulphate, and evaporated to dryness in vacuo. The crude product was purified on silica gel (eluent: methylene chloride:ethyl acetate (95:5) to give 4-[2-(tert-butoxycarbonylamino)benzyl]phthalic acid dimethyl ester as yellow crystals (yield: 1.49 g, (40%)). 1H—NMR (CDCl3) in ppm: δ 7.70 (1H,d); 7.67 (1H,d); 7.47 (1H,d); 7.22-7.33 (2H,m); 7.10 (2H,d); 6.05 (1H,s); 4.03 (2H,s); 3.9 (6H,2xs); 1.47 (9H,s).

1. temperatureThe reaction mixture was cooled to room temperature
2. customThe organic phase was isolated
3. washwashed with water (2×50 ml)
4. dry with materialdried over magnesium sulphate
5. customevaporated to dryness in vacuo
6. customThe crude product was purified on silica gel (eluent