Carbon tetrabromide → 4-(4-Bromomethyl-phenoxymethyl)-5-methyl-2-phenyl-oxazole

HRID 644006

Reaktionsgleichung

Reaktionsgleichung von HRID 644006
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=1.C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:24][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 110228074-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

Produkt 1

HCID 685799434-(4-Bromomethyl-phenoxymethyl)-5-methyl-2-phenyl-oxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of the title C compound, [4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-methanol (1.5 g, 5.08 mmol), carbon tetrabromide (2.53 g, 7.62 mmol), and triphenylphosphine (2.0 g, 7.62 mmol) in DCM is stirred at RT overnight. The mixture is then concentrated under vacuum, and chromatographed on a silica gel column using 8% EtOAc in hexane as the eluent to give 4-(4-bromomethyl-phenoxymethyl)-5-methyl-2-phenyl-oxazole as a white solid.

Aufarbeitung

  1. concentrationThe mixture is then concentrated under vacuum
  2. customchromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-540e8877a2444e27b15bf537cc4fdcf5
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700637B2

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