Isobutanol → 4-Bromo-2-(2-methylpropoxy)benzoic acid

Reaktionsgleichung

[H-].[Na+].[CH3:3][CH:4]([CH3:7])[CH2:5][OH:6].[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11](F)[CH:10]=1>CN(C)C=O>[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:6][CH2:5][CH:4]([CH3:7])[CH3:3])[CH:10]=1

Komponenten

Versuchsvorschrift

To a suspension of sodium hydride (60% w/w, 20.5 g) in N,N-dimethylformamide (365 ml) was added 2-methyl-1-propanol (48.7 ml) dropwise below 30° C. over 2 hours under nitrogen atmosphere. To the mixture was added 4-bromo-2-fluorobenzoic acid (50.0 g) slowly below 35° C. To the reaction mixture was added N,N-dimethylformamide (600 ml) and the mixture was stirred at room temperature for 4 days. The reaction mixture was partitioned between water (2000 ml) and hexane (1000 ml). The water layer was separated and acidified with 37% hydrochloric acid. The precipitate was collected by filtration, washed with water and dried at 55° C. to give 4-bromo-2-isobutoxybenzoic acid (62.4 g) as a white solid.