Reaktion #409225

Reaktionsgleichung

methylene chloride hexane

benzyl bromide

potassium carbonate

hydrochloric acid ethyl acetate

→

oil

Ausbeute 63.0%

4-Bromo-5,6,7.8-tetrahydro-1-benzyloxynaphthalene

Ausbeute 63.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed 14 hours
2. 2
   TemperaturThe reaction was cooled
3. 3
   Sonstigethe organic layer separated
4. 4
   Waschenwashed with water and brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was chromatographed on silica gel

Vorschrift

The above oil was dissolved in 100 mL acetonitrile, and treated with 3.57 mL (30 mmol) benzyl bromide and 5.53 g (40 mmol) potassium carbonate, then refluxed 14 hours. Thin layer chromatography (TLC) showed a major spot at Rf=0.3 in 10% methylene chloride/hexane (with benzyl bromide at Rf=0.4). The reaction was cooled, poured into dilute aqueous hydrochloric acid/ethyl acetate, and the organic layer separated, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methylene chloride/hexane as eluant to afford 4.0 g (63%) of an oil. 1H-NMR (δ, CDCl3): 1.77 (m, 4H), 2.75 (m, 4H), 5.045 (s, 2H), 6.62 (d, J=9, 1H), 7.3-7.5 (m, 6H); 13C-NMR (δ, CDCl3): 22.2, 22.9, 24.0, 30.7, 69.9, 109.8, 116.7, 127.1, 127.9, 128.6, 129.1, 129.3, 137.2, 137.5, 155.6.

Quelle