N-bromobutanimide → 4-(Bromomethyl)-2-methoxy-5-(4-methoxyphenyl)pyridine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][N:4]=1.C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:9][C:7]1[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
According to Scheme 31 Step 2: To a solution of 2-methoxy-5-(4-methoxyphenyl)-4-methylpyridine (2.20 mmol, 0.50 g, Example 48 Step 1) in CCl4 (10 mL) was added NBS (2 eq, 4.40 mmol, 0.78 g). The reaction was then heated to reflux and subjected to UV light for 48 hours. The reaction was allowed to cool, filtered and concentrated under reduced pressure to afford crude 4-(bromomethyl)-2-methoxy-5-(4-methoxyphenyl)pyridine (0.70 g) as a yellow oil which was used without any purification in the next step.