Boron tribromide → HCID 19040960, compound
Reaction equation
C[O:2][C:3]1[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][C:4]=1[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:4]=1[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of 2,4-dimethoxy-N-(1-methylethyl)-N-phenylbenzamide (2.4 g, 8.03 mmol) in 10 ml of dichloromethane at 0° C. was treated with 1N boron tribromide (33.2 mL, 33.2 mmol) and stirred at room temperature for 1 hour. The reaction is poured in to the ice water. After stirring for 15 minutes, the reaction was partitioned between ethyl acetate and brine, dried over magnesium sulfate and concentrated in vacuo to afford yellow foam. This material is purified by chromatography on silica gel (70 g) with 3-5% methanol/dichloromethane as the eluent to afford 2,4-dihydroxy-N-(1-methylethyl)-N-phenylbenzamide as colorless foam.