Boron tribromide → 2-(4-Diethylcarbamoylbenzyl)phenol
Reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]C)=[CH:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:21]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:8][CH:7]=1)=[O:5])[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The obtained 2-(4-diethylcarbamoylbenzyl)anisole was dissolved in dichloromethane (280 ml), added with boron tribromide (25.0 g) and stirred at room temperature for 3 hours. After the reaction mixture was slowly poured into ice (300 g) with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with dichloromethane (300 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1) to obtain 10.15 g of the title compound. Yield: 79% (for the three steps).