Reaktion #595848

Reaktionsgleichung

K2CO3

2-(1-adamantyl)-4-bromo-5-methylphenol

benzyl bromide

→

5-(1-adamantyl)-4-benzyloxy-2-methylphenyl bromide

Ausbeute 91.8%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux for 24 h under argon
3. 3
   SonstigeAcetone was removed at reduced pressure
4. 4
   workup.ADDITION2 N HCl (80 mL) was added
5. 5
   ExtraktionThe mixture was extracted with EtOAc (300 mL)
6. 6
   Waschenthe organic layer was washed with H2O and brine
7. 7
   Sonstigedried
8. 8
   SonstigeAfter removal of solvent
9. 9
   Sonstigethe residue was purified by chromatography on a silica gel

Vorschrift

To a solution of 2-(1-adamantyl)-4-bromo-5-methylphenol (6.53 g, 20.34 mmol) in acetone (65 mL) was added benzyl bromide (3.48 g, 20.34 mmol) followed by K2CO3 (3.51 g, 25.43 mmol). The mixture was stirred and heated at reflux for 24 h under argon. Acetone was removed at reduced pressure, and then 2 N HCl (80 mL) was added. The mixture was extracted with EtOAc (300 mL), and the organic layer was washed with H2O and brine and dried. After removal of solvent, the residue was purified by chromatography on a silica gel using hexane to give 7.68 g (80%) of 5-(1-adamantyl)-4-benzyloxy-2-methylphenyl bromide as a white solid, mp 138-139° C. IR 2903, 2848, 1163 cm−1; 1H NMR (CDCl3) δ 1.71 (bs, 614, AdCH2), 2.02 (bs, 3H, AdCH), 2.08 (bs, 6H, AdCH2), 2.33 (s, 3H, CH3), 5.07 (s, 2H, C6H5CH2), 6.80 (s, 1H, 3-ArH), 7.33 (s, 1H, 6-ArH), 7.3-7.5 ppm (m, 5H, C6H5).

Quelle