Reaktion #699801

Reaktionsgleichung

allyl bromide

K2CO3

3-methoxy-4-bromo-phenol

→

title compound

1-Bromo-2-methoxy-4-allyloxybenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture is heated
2. 2
   FiltrationThe mixture is filtered
3. 3
   Einengenthe filtrate is concentrated on the rotovap
4. 4
   SonstigeThe residue is partitioned between Et2O and H2O
5. 5
   SonstigeThe Et2O layer is separated
6. 6
   Extraktionextracted with 2×70 ml 5% NaOH
7. 7
   Waschenwashed with brine
8. 8
   Trocknendried (MgSO4)
9. 9
   Filtrationfiltered
10. 10
    SonstigeEvaporation on the rotovap

Vorschrift

To a stirred mixture of K2CO3 (3.45 g, 0.025 mol), and 3-methoxy-4-bromo-phenol (6.09 g, 0.030 mol) at ambient temperature under argon is added allyl bromide (3.60 g, 0.030 mol). The resulting mixture is heated and stirred overnight. The mixture is filtered and the filtrate is concentrated on the rotovap. The residue is partitioned between Et2O and H2O. The Et2O layer is separated and extracted with 2×70 ml 5% NaOH, washed with brine, dried (MgSO4) and filtered. Evaporation on the rotovap followed by flash chromatography (EtOAc-hexane 1:9) gives 5.93 (81%) of the title compound. Rf-0.41 (EtOAc-hexane 25:75) HNMR (CDCl3) d 7.38 (d, 1H), 6.38 (dd, 1H) 6.1-5.9 (m, 1H), 5.41 (d, 1H), 5.29 (d, 1H), 4.51-4.48 (m, 2H), 3.84 (s, 3H).

Quelle