Reaktion #595852

Reaktionsgleichung

4-bromo-1,2-methylenedioxybenzene

1-adamantanol

MeSO3H

→

4-(1-adamantyl)-6-bromobenzo[1,3]dioxole

Ausbeute 86.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting solution was quenched with H2O (40 mL)
2. 2
   Extraktionextracted with EtOAc (110 mL)
3. 3
   WaschenThe extract was washed with 0.5 N NaOH, sat. NaHCO3, and brine
4. 4
   Sonstigedried
5. 5
   SonstigeThe residue obtained on concentration
6. 6
   Sonstigewas purified on silica gel (hexane)

Vorschrift

A mixture of 4-bromo-1,2-methylenedioxybenzene (2.00 g, 9.95 mmol), 1-adamantanol (1.52 g, 9.95 mmol), and MeSO3H (5 mL) was stirred for 1 h. The resulting solution was quenched with H2O (40 mL) and extracted with EtOAc (110 mL). The extract was washed with 0.5 N NaOH, sat. NaHCO3, and brine and dried. The residue obtained on concentration was purified on silica gel (hexane) to give 2.86 g (86%) of 4-(1-adamantyl)-6-bromobenzo[1,3]dioxole as a white solid, mp 135-136° C. IR 2901, 2843, 1435, 1189 cm−1; 1H NMR δ (CDCl3) 1.76 (bs, 6H, AdCH2), 1.98 (bs, 6H, AdCH2), 2.06 (bs, 3H, AdCH), 5.93 (s, 2H, CH2), 6.84 (s, 1H, 7-ArH), 6.86 ppm (s, 1H, 5-ArH).

Quelle