p-Toluenesulfonic acid → 2-(3-Bromo-4-methylphenyl)-1,3-benzoxazole

HRID 7688

Reaktionsgleichung

Reaktionsgleichung von HRID 7688
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]=2)[CH:15]=[CH:16][C:17]=1[CH3:18]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 219909653-bromo-N-(2-hydroxyphenyl)4-methylbenzamide

Produkt 1

HCID 219909962-(3-Bromo-4-methylphenyl)-1,3-benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide (554 mg, 1.8 mmol), p-toluenesulfonic acid (2.41 g, 12.7 mmol) and toluene (50 mL) was refluxed for 4 h, cooled to rt, and filtered through a Celite pad. The filtrate was evaporated to dryness and the residue was purified by flash chromatography on silica gel using a gradient of EtOAc:hexanes (0 to 30 min:0 to 15% EtOAc) to afford 2-(3-bromo-4-methylphenyl)-1,3-benzoxazole as a colorless solid. MS (ESI) 288 (M+).

Aufarbeitung

  1. temperaturewas refluxed for 4 h
  2. filtrationfiltered through a Celite pad
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified by flash chromatography on silica gel using a gradient of EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-0f114aa097314311987a9195a28a0016
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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