Benzoyl Peroxide → Methyl 2-(bromomethyl)-4-(5,6-dimethoxy-3-pyridyl)-6-methylbenzoate

HRID 1259341Notes

Reaction equation

HRID 1259341 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[C:19]([CH3:21])[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:22])[CH:12]=2)[CH:6]=[N:7][C:8]=1[O:9][CH3:10].C([O-])([O-])=O.[K+].[K+].C1C(=O)N([Br:36])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:36][CH2:21][C:19]1[CH:20]=[C:11]([C:5]2[CH:6]=[N:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:12]=[C:13]([CH3:22])[C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 66743002Methyl 4-(5,6-dimethoxy-3-pyridyl)-2,6-dimethylbenzoate

Product 1

HCID 66743158Methyl 2-(bromomethyl)-4-(5,6-dimethoxy-3-pyridyl)-6-methylbenzoateYield 76.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

As shown in step 6-ii of Scheme 6, Compound 2022 (710 mg, 2.36 mmol) was dissolved in CCl4 (20 mL) and K2CO3 (651 mg, 4.71 mmol), NBS (461 mg, 2.59 mmol), and benzoyl peroxide (57 mg, 0.24 mmol) were added. The reaction mixture was heated to reflux for 4 hours. After cooling to room temperature, the reaction mixture was filtered and the solid washed with CCl4. The filtrate was concentrated to an oil under reduced pressure and purified by silica gel chromatography to provide methyl 2-(bromomethyl)-4-(5,6-dimethoxy-3-pyridyl)-6-methyl-benzoate (Compound 2023, 685 mg, about 70% pure). This compound was used in subsequent reactions as is.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe reaction mixture was filtered
  4. washthe solid washed with CCl4
  5. concentrationThe filtrate was concentrated to an oil under reduced pressure
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-59fd9b618f9f4702a65435e8c9c3a0ab
Source dataset
uspto-grants-2013_06
Patent number
US08466288B2

Reaction notes

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