反应详情

Sparge a mixture of 5-methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (2.0 g, 9.7 mmol) (prepared as described in Journal of Organic Chemistry, 53 (8) 1768-1774 (1988)), 2-bromobenzonitrile ((1.77 g, 9.7 mmol), NaOAc (1 g, 12 mmol) and dimethylacetamide (100 mL) with nitrogen for 15 minutes. Add Hermann catalyst (320 mg, 0.46 mmol)(Chem. Eur. J. 1357-1364 (1997)) and heat at 150° C. for 6 days. Cool the reaction and partition between water (1 L) and EtOAc (500 mL). Wash the organic layer with water (3×1L). Dry (MgSO4) and concentrate under reduced pressure to give 3.3 g brown oil. Purify on silica gel using EtOAc/hexane 500 mg nitrile that is 81% pure by glc. Recrystallize (EtOH) to give 213 mg (7%) pale yellow plates, mp 185.4° C. 1H NMR (CDCl3) δ 3.04 (br d, 2H), 3.47 (br s, 2H), 6.82-7.34 (m, 11H), 7.62 (m, 2H); MS (ES) 308 (M+1). HPLC shows 98% purity.

1. customSparge
2. temperatureCool
3. customthe reaction
4. custompartition between water (1 L) and EtOAc (500 mL)
5. washWash the organic layer with water (3×1L)
6. dry with materialDry (MgSO4)
7. concentrationconcentrate under reduced pressure