Benzoyl Peroxide → 2-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

HRID 7732

Reaktionsgleichung

Reaktionsgleichung von HRID 7732
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:6]=[CH:7][C:8]=1[CH3:9].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:37][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 219909682-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole

Produkt 1

HCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

2-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole (1.0 g, 4.1 mmol), carbon tetrachloride (18 mL), benzoyl peroxide (66 mg, 0.3 mmol) and N-bromosuccinimide (970 mg, 5.4 mmol) was heated to reflux conditions under argon and placed under a UV light. After 1 h, no starting material was observed by TLC. After cooling mixture to rt, filtered, washing with dichoromethane. After concentrating filtrate in vacuo, the resulting colorless solid was purified by flash chromatography, using a gradient elution of 1:4 EtOAc:hexanes to EtOAc. This afforded the desired intermediate, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole, as a colorless solid.

Aufarbeitung

  1. temperatureto reflux conditions under argon
  2. filtrationfiltered
  3. washwashing with dichoromethane
  4. concentrationAfter concentrating filtrate in vacuo
  5. customthe resulting colorless solid was purified by flash chromatography
  6. washa gradient elution of 1:4 EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-7b5dc4ac04c6402099cfcfbd4e02fa1a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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