Methanol → [3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester
反応式
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[C:4]([CH:19]=[O:20])[CH:3]=1.S(Cl)(Cl)=O.[CH3:25]O>>[CH3:25][O:15][C:14](=[O:16])[CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][C:4]=2[CH:19]=[O:20])[CH:8]=1参加物
4
反応条件
- 温度
- 65 °C
実験手順
To [3-(4-bromo-2-formyl-phenoxy)-phenyl]-acetic acid (1 g, 3.0 mmol) in MeOH (10 mL) was added thionyl chloride (0.43 mL, 6.0 mmol), and the reaction was heated to 65° C. for 2 hours, and then at room temperature overnight. The mixture was quenched with 1N aqueous NaOH and extracted three times with EtOAc, and the combined organic layers were washed with H2O, dried, and concentrated. The residue was purified by silica gel chromatography (20-40% EtOAc in hexanes) to give the desired product (0.7 g); as well as the acetal by-product.