Hydrochloric Acid → HCID 178419536, compound

Participants

Reaction Steps

Following a general procedure for preparing 24 (Creager et al. (1994) J. Electroanal. Chem., 370: 203–211), to a freshly prepared zinc/mercury amalgam (6.7 g granulated Zn, 0.4 g HgCL2) in a 100 mL flask was added 10 M HCl (40 mL) with stirring. A solution of 22 (3.0 g, 6.7 mmol) in toluene (40 mL) was added in one portion. The resulting two-phase mixture was heated to reflux and stirred vigorously. After 16 h under reflux, during which two 5 mL portions of 10 M HCl were added, the reaction flask was cooled to rt. The phases were separated, and the organic layer was washed with water (3×100 mL) and dried (MgSO4). The solvent was evaporated in vacuo and the residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:1) to afford a brown oil (2.6 g, 90%) that solidified upon standing in the freezer: mp 40–42° C.; 1H NMR δ 1.29 (s, 16H), 1.47 (m, 2H), 1.86 (m, 2H), 2.32 (m, 2H), 3.42 (m, 2H), 4.05 (s, 2H), 4.06 (s, 2H), 4.10 (s, 5H); 13C NMR δ 28.2, 28.8, 29.5, 29.6, 31.1, 32.9, 34.0, 67.0, 68.1, 68.5, 89.6; FAB-MS obsd 432.1114, calcd exact mass 432.1115 (C22H33BrFe).

Provenance & Evidence