Bromine → 2-Bromo-1-(2,3-dihydrobenzofuran-6-YL)ethan-1-one
Reaktionsgleichung
[Br:1]Br.[O:3]1[C:7]2[CH:8]=[C:9]([C:12](=[O:14])[CH3:13])[CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4]1>CO>[Br:1][CH2:13][C:12]([C:9]1[CH:10]=[CH:11][C:6]2[CH2:5][CH2:4][O:3][C:7]=2[CH:8]=1)=[O:14]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Br2 (0.36 ml, 7.01 mmol) was added dropwise to a stirring solution of 1-(2,3-dihydro-benzofuran-6-yl)-ethanone (1.13 g, 6.97 mmol) in MeOH (20 mL) held at 0° C. The reaction mixture was slowly allowed to reach room temperature. After 3 h, the reaction was quenched by the addition of NaHCO3 (aq, saturated)(until pH=8). Most of the methanol was removed under reduced pressure and the residue was extracted twice with EtOAc (2×20 mL). The organic extracts were pooled, washed with brine (10 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC using a gradient of 40-70% MeCN in a 0.1M ammonium acetate buffer as eluent. The fractions containing the desired product were pooled and most of the MeCN was removed under reduced pressure. The residue was extracted with EtOAc (2×20 mL) and the combined organic layers was washed with brine, dried over MgSO4 and concentrated. The obtained was finely washed MeOH to give the title compound.