HCID 86677590, compound → HCID 67323924, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12](=[O:17])N(OC)C)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:18][Mg]Cl>C1COCC1>[C:12]([C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Br:1])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:17])[CH3:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The compound methyl 3-bromo-5-(methoxy(methyl)carbamoyl)benzoate (2.3 g, 7.6 mmol) was dissolved in dry THF (50 mL), solution was cooled to 0° C. and methylmagnesium chloride (3M in THF, 2.5 mL, 7.6 mmol)) was added dropwise. The reaction mixture was slowly allowed to come to room temperature and stirred further for 6 h. The reaction mixture was cooled to 0° C. and quenched with saturated NH4Cl solution. The product was extracted with EtOAc. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluent 5% EtOAc in petroleum ether) to get methyl 3-acetyl-5-bromobenzoate (0.95 g, yield 49%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.51 (t, J=1.3 Hz, 1H), 8.37 (t, J=1.7 Hz, 1H), 8.28 (t, J=1.6 Hz, 1H), 3.97 (s, 3H), 2.65 (s, 3H).