反应详情

A solution of 5-allyl-2-bromo-1,3-dimethylbenzene (1.0 g) is cooled to 0° C., 9-borabicyclo[3.3.1]nonane (9-BBN, 26 mL of a 0.5 M solution in tetrahydrofurane) is added dropwise and the mixture is stirred for 2 hours at room temperature. After cooling to 0° C. NaOH (6.7 mL, 4 M) and H2O2 (6.7 mL, 35%) are added dropwise. The mixture is stirred for 12 hours while warming to room temperature. Then the mixture is partitioned between brine and diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→70:30) to give the title compound. Yield: 750 mg; LC (method 8): tR=0.28 min; Mass spectrum (ESI+): m/z=260 [M+NH4]+.

1. temperatureAfter cooling to 0° C
2. stirringThe mixture is stirred for 12 hours
3. temperaturewhile warming to room temperature
4. customThen the mixture is partitioned between brine and diethylether
5. dry with materialThe organic phase is dried (MgSO4)
6. concentrationconcentrated
7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→70:30)