反应详情

A mixture of dimethyl 5-hydroxyisophthalate (3.1 g, 14.75 mmol), 4-fluorophenylboronic acid (4.13 g, 29.5 mmol), copper(II) acetate (2.68 g, 14.75 mmol) and triethylamine (4.48 g, 44.2 mmol) in CH2Cl2 (65 mL) was stirred at rt in the open air for 38 h. An additional 1 g of fluorophenylboronic acid was added and the reaction mixture was continued to stir at rt in the open air. After 24 h, an additional 1 g of fluorophenylboronic acid and 300 mg of copper acetate were added to the reaction mixture and it was continued to stir for 6 h in the open air. The mixture was mixed with CHCl3 and aq HCl, the organic layer was separated, washed with aq HCl, aq NaHCO3, dried over MgSO4, concentrated, and the residue was purified by flash column chromatography on SiO2 eluting with Hexane:EtOAc:MeOH/800:200:40 to obtain the desired product (3.8 g, 12.49 mmol, 85% yield) as a white solid. 1H NMR (CDCl3): δ 8.36 (s, 1H), 7.75 (s, 2H), 7.06˜6.96 (m, 4H), 3.89 (s, 6H).

1. stirringto stir at rt in the open air
2. waitAfter 24 h
3. stirringto stir for 6 h in the open air
4. customthe organic layer was separated
5. washwashed with aq HCl, aq NaHCO3
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customthe residue was purified by flash column chromatography on SiO2 eluting with Hexane