Water → 6-Fluoro-2-hydroxy-3-methoxybenzaldehyde

反応式

B(Cl)(Cl)Cl.[F:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([O:14]C)[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1.O>ClCCl>[F:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([OH:14])[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1

参加物

実験手順

1M boron trichloride in dichloromethane (25 ml; 25 mmol) was added to a solution of 6-fluoro-2,3-dimethoxy-benzaldehyde [Cantrell, Amanda S.; Engelhardt, Per; Hoegberg, Marita; Jaskunas, S. Richard; Johansson, Nils Gunnar; et al.; J. Med. Chem.; 39; 21; 1996; 4261-4274] (4.26 g; 23 mmol) in dichloromethane (30 ml) keeping the reaction temperature at −70 C. The reaction mixture stirred at room temperature overnight and hydrolyzed with water. The organic phase was separated, washed with water and evaporated in vacuc. The residue was chromatographed (silica gel, EA:Hex, 5:1) to give 3.72 g (94%) of 6-fluoro-2-hydroxy-3-methoxy-benzaldehyde as yellow crystals.