反应详情

温度

0 °C

To a mixture of 2-(1-adamantyl)-4-bromophenol (10.00 g, 32.57 mmol) in DMF (90 mL) cooled to 0° C. was added NaH (1.08 g, 80% in mineral oil, 35.83 mmol) under an atmosphere of argon. The mixture was allowed to warm to room temperature and subsequently stirred for 30 minutes. The resulting mixture was cooled to 0° C. and chloromethyl methyl ether (2.72 mL, 35.83 mmol) was added dropwise. After 14 hours at room temperature and the reaction mixture was poured into ice water and extracted with EtOAc (2×150 mL). The combined organic layers were washed water (100 mL), brine (100 mL), dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the resulting solid was purified on silica gel (hexane:ethyl acetate 99:1 to 97:3) to give 8.6 g (76%) of 3-(1-adamantyl)-4-methoxymethoxy-bromobenzene. 1H NMR (300 MHz; CDCl3): δ 1.77 (s, 6H), 2.08 (s, 9H), 3.50 (s, 3H), 5.19 (s, 2H), 6.98 (d, J=8.7 Hz, 1H), 7.24 (dd, J1=9.0 Hz, J2=2.4 Hz, 1H), 7.32 (d, J=2.4 Hz, 1H).

1. temperatureto warm to room temperature
2. temperatureThe resulting mixture was cooled to 0° C.
3. waitAfter 14 hours at room temperature
4. extractionextracted with EtOAc (2×150 mL)
5. washThe combined organic layers were washed water (100 mL), brine (100 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customThe solvent was removed under reduced pressure
9. customthe resulting solid was purified on silica gel (hexane:ethyl acetate 99:1 to 97:3)