反应详情

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).

1. customThe resulting solution was quenched with H2O (40 mL)
2. extractionextracted with EtOAc (110 mL)
3. washThe extract was washed with 0.5 N NaOH, sat. NaHCO3, and brine
4. customdried
5. customThe residue obtained on concentration
6. customwas purified on silica gel (hexane)