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

HRID 1259341
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259341
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 66743158Methyl 2-(bromomethyl)-4-(5,6-dimethoxy-3-pyridyl)-6-methylbenzoateAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-59fd9b618f9f4702a65435e8c9c3a0ab
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466288B2

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