Reaktion #157486

Reaktionsgleichung

4-bromo-3-methylphenol

N-Boc aminoethanol

PPh3

DIAD

→

title compound

1,1-Dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate

Lösungsmittel

PhH

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed (2×satd Na2CO3, 2×H2O, brine)
2. 2
   Trocknendried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by flash chromatography (EtOAc/hexanes)

Vorschrift

To a solution of 4-bromo-3-methylphenol (0.187 g; 1.00 mmol), N-Boc aminoethanol (0.39 mL; 2.5 mmol) and PPh3 (0.655 g; 2.5 mmol) in anhyd PhH (5 mL) at 0° C. was added DIAD (0.49 mL; 2.5 mmol), dropwise over 15 min. The mixture was stirred 16 h at room temperature, diluted with Et2O, washed (2×satd Na2CO3, 2×H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum, which solidified on standing. LC/MS (method A) tR 2.95 min, m/z 330, 332 (M+H, Br isotopes, 2%), 352, 354 (M+Na, Br isotopes, 40-43%), 230, 232 ([M-Boc]+H, Br isotopes, 100%).

Quelle