Reaktion #7810

ord-3fbdb02c28694b2ab3cd6d303a6d36e5

Reaktionsgleichung

COCOc1cc(-c2nc3ccccc3o2)ccc1C
2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole
O=C1CCC(=O)N1Br
NBS
O=C(OOC(=O)c1ccccc1)c1ccccc1
benzoyl peroxide
COCOc1cc(-c2nc3ccccc3o2)ccc1CBr
2-[4-(bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeCCl4 was removed in vacuo and residue
  2. 2
    Sonstigewas purified by flash column (silica gel, hexanes:EtOAc 5:1)

Vorschrift

A solution of 2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole (200 mg, 0.74 mmol, 84%), NBS (179 mg, 0.81 mmol), and benzoyl peroxide (50 mg) in CCl4 (10 mL), was refluxed for 12 h. After cooling to rt, CCl4 was removed in vacuo and residue was purified by flash column (silica gel, hexanes:EtOAc 5:1) to afford 2-[4-(bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole. MS (ESI) 349 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087601B2uspto-grants-2006_08