Boron tribromide → HCID 18456631, compound
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[C:10]([NH:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])[C:10]([NH:12][CH3:13])=[O:11])=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(4-methoxy-phenyl)-N-methyl-2-oxo-acetamide (74a) (1.35 g, 6.99 mmol) in 25 mL of CH2Cl2 was added 1.0 M BBr3 in CH2Cl2 (14 mL, 28.0 mmol) at 0° C. The mixture was stirred at 0° C. to room temperature for two hours. The reaction was quenched with MeOH, neutralized with concentrated aqueous NH4OH to pH ˜7. The resulting mixture was stirred at room temperature for one hour. Water was added, and the mixture was extracted with CH2Cl2. The organic phase was dried over Na2SO4, concentrated, and purified by flash column chromatography eluting with 1:1 EtOAc and hexanes to provide 0.53 g off-white solid as the intermediate 74b. 1H NMR (300 MHz, CD3OD) δ 7.03 (d, 2H, J=8.86 Hz), 6.75 (d, 2H, J=8.86 Hz), 2.76 (s, 3H). LCMS (ESI+) [M+Na]/z Calc'd 202, found 202.