Benzoyl Peroxide → HCID 18421399, Verbindung

HRID 1281642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281642
[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:18])=[C:10]([CH3:17])[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:18])=[C:10]([CH2:17][Br:19])[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 854734(3,4,8-trimethyl-2-oxochromen-7-yl) acetate

Produkt 1

HCID 18421399HCID 18421399, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 7-acetoxy-3,4,8-trimethylcoumarin (6.22 g, 25.3 mmol), N-bromosuccinimide (4.61 g, 25.9 mmol) and benzoyl peroxide (390 mg) were refluxed in carbon tetrachloride for 3.5 hours. The mixture was cooled to room temperature and partitioned between CH2Cl2 and water. The organic layer was separated and washed with water several times, then washed with brine. The organic layer was then dried with anhydrous sodium sulfate and evaporated to give crude product (11.8 g) which was recrystallized twice in toluene to give 7-acetoxy-3-bromomethyl-4,8-dimethylcoumarin, a white crystalline solid (4.86 g, 59%). 1H NMR (CDCl3): δ7.54 (d; J=8.8 Hz, 1H), 7.05 (d, J=8.8 Hz, 1H), 4.57 (s, 2H), 2.50 (s, 3H), 2.37 (s, 3H), 2.28 (s, 3H).

Aufarbeitung

  1. custompartitioned between CH2Cl2 and water
  2. customThe organic layer was separated
  3. washwashed with water several times
  4. washwashed with brine
  5. dry with materialThe organic layer was then dried with anhydrous sodium sulfate
  6. customevaporated
  7. customto give crude product (11.8 g) which
  8. customwas recrystallized twice in toluene

Quellen und Nachweise

ORD-Eintrag
ord-04952936b8da48c48025c43cd2dc3d17
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455286B1

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