2,4-Dichlorobenzaldehyde → (2,4-Dichloro-phenyl)-3-methyl-butan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) stirred solution of 2,4-dichlorobenzaldehyde (2 g, 11.43 mmol) in THF (50 ml) under N2 is added isobutyllithium (7.86 ml, 12.57 mmol) slowly and the reaction is stirred at RT over the weekend. The reaction mixture is added to sat. ammonium chloride (100 ml) and extracted with EtOAc (140 ml). The organic portion is washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by chromatography on silica (70 g/150 ml silica-column) eluting with 10% EtOAc/iso-hexane to give (2,4-dichloro-phenyl)-3-methyl-butan-1-ol as a yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.53 (1H, d, J 8.3), 7.36 (1H, d, J 2.0), 7.29 (1H, dd, J 8.3, 2.0), 5.18 (1H, dd, J 9.2, 3.7), 1.88 (1H, m), 1.61 (1H, ddd, 14.0, 9.2, 4.7), 1.52 (1H, ddd, 14.0, 9.1, 3.7), 1.03 (3H, d, J 6.6), 0.99 (3H, d, J 6.6).

Provenance & Evidence