N-bromobutanimide → 5-bromo-6-(4-fluorophenyl)-7-methyl-2,3-dihydro-1H-pyrrolizine

참여 물질

반응 단계

The solution of 6-(4-fluorophenyl)-7-methyl-2,3-dihydro-1H-pyrrolizine (9.0 g, 42 mmol) in abs. THF (50 ml) is cooled to −15° C. N-Bromosuccinimide (3.46 g, 19.4 mmol) is added in portions; the mixture is stirred until no more starting material is detectable (TLC SiO2, diisopropyl ether-hexane 2:1). The black-purple-coloured reaction mixture is chromatographed on a column (20 cm×3 cm) packed with Al2O3 (ICI, for dry packing). The column is subsequently washed with n-hexane (80 ml), and the filtrates are concentrated. 3.55 g (28.9%) of a black-brown oil are obtained, which rapidly decomposes.

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