Carbon Tetrachloride → Benzoxazole

HRID 7737

Reaktionsgleichung

Reaktionsgleichung von HRID 7737
COC1C=C([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)C=C(OC)C=1C.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.BrN1C(=O)CCC1=O>CCOC(C)=O>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[CH:12]1

Komponenten

6

Edukt 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 219909742-(3,5-Dimethoxy-4-methylphenyl)-1,3-benzoxazole

Produkt 1

HCID 9228Benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-(3,5-dimethoxy-4-methylphenyl)-1,3-benzoxazole (260 mg, 1 mmol), carbon tetrachloride (4.2 mL), benzoyl peroxide (15 mg, 0.06 mmol) and N-bromosuccinimide (270 mg, 1.5 mmol) was heated to reflux conditions under argon overnight. Concentration of cooled reaction mixture in vacuo afforded a yellow solid. Flash chromatography on silica gel of crude material using 1:4 EtOAc:hexanes gave the desired intermediate, 2-[4-bromomethyl)-3,5-dimethoxyphenyl]-1,3-benzoxazole, as a colorless solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux conditions under argon overnight
  3. customConcentration of cooled reaction mixture in vacuo
  4. customafforded a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-394150f62b5b4dda8aa07bbea70ff52f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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