4-bromo-N-methoxy-N,3-dimethylbenzamide → 1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-one
Reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][C:3]=1[CH3:14]>O1CCCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH2:12][CH2:13][CH2:2][CH:3]([CH3:14])[CH3:4])=[CH:4][C:3]=1[CH3:14]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-Bromo-N-methoxy-3,N-dimethyl-benzamide (5.94 g, 23.05 mmol) was suspended in anhydrous tetrahydrofuran (200 mL), and cooled to 0° C. with stirring under nitrogen. 1-magnesium bromo-4-methyl-pentane (23 mL, 1.5M in tetrahydrofuran, 34.8 mmol) was slowly added to the reaction over 1 h. The reaction was allowed to warm slowly to room temperature and monitored by TLC. Upon complete consumption of starting material, the reaction was carefully neutralized with 1N hydrochloric acid, extracted with diethyl ether, washed, dried, and concentrated. The 1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-one (5.2 g, 18.4 mmol) 80% yield, was used without further purification.