N-bromobutanimide → 4-(Bromomethyl)-2-methoxy-5-(4-methoxyphenyl)pyridine

HRID 1948271Notes

Reaction equation

HRID 1948271 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]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69344963HCID 69344963, compound

Product 1

HCID 693453274-(Bromomethyl)-2-methoxy-5-(4-methoxyphenyl)pyridineYield 103.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

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.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7bd0ffc02974cc59284b6965293961f
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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