Reaktion #945823

Reaktionsgleichung

water

2-ethyl-4-bromophenol

ethylene carbonate

potassium carbonate

→

product

Ausbeute 82.1%

2-(4-Bromo-2-ethyl-phenoxy)-ethanol

Ausbeute 82.1%

Lösungsmittel

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintained for 3 h
2. 2
   TemperaturThe reaction was cooled
3. 3
   Extraktionextracted with EtOAc (2×100 mL)
4. 4
   WaschenThe combined organics were washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by flash column chromatography (10–20% EtOAc in hexanes)

Vorschrift

To a solution of 2-ethyl-4-bromophenol (3.5 g, 17.4 mmol) and ethylene carbonate (3.22 g, 37 mmol) in NMP (60 mL) was added potassium carbonate (5.17 g, 37.4 mmol). The resulting mixture was heated to 125° C. and maintained for 3 h. The reaction was cooled and poured into water (250 mL) and extracted with EtOAc (2×100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (10–20% EtOAc in hexanes) to give the product (3.5 g, 82% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ: 1.19 (t, J=7.6 Hz, 3 H), 1.89 (brs, 1 H), 2.61 (q, J=7.6 Hz, 2 H), 4.05 (m, 4 H), 6.70 (d, J=8.7 Hz, 1 H), 7.24 (m, 2 H).

Quelle