2-(4-Bromophenyl)-1,3-dioxolane → HCID 86607749, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.65 g (6 mmol) of N-4-butylphenyl-N-3-methylthiophenylamine (3), 2.04 g (5.3 mmol) of 2-(4-bromophenyl)-[1,3]dioxolane (4), 23 mg (0.025 mmol) of Pd2(dba)3, 42 mg (0.075 mmol) of DPPF and 1.34 g (14 mmol) of t-BuONa in 20 mL of toluene was stirred for 24 h at 90° C. The reaction mixture was allowed to cool down to room temperature and was diluted with 150 mL diethyl ether. After filtration, the solvent was evaporated and the residue was purified by liquid chromatography on silica gel. The product was then dissolved in 20 mL of THF and 10 mL of 10% HCl was added. After stirring for 12 h at room temperature, the mixture was diluted with 150 mL of chloroform, washed twice with equal amounts of sat. NaHCO3 aqueous solution and once with water. The organic phase was dried over MgSO4, evaporated and the crude product was filtered over a short column of silica gel with chloroform. 1H-NMR (400 MHz, CDCl3): δ 7.67 (m, 2 H), 7.245 (m, 1 H), 7.16 (m, 2H), 7.07(m, 2), 7.05 (m, 1 H), 7.03-6.99 (m, 3 H), 2.617 (t, J=7.6 Hz, 2H), 2.42 (s, 3 H), 1.62 (m, 2 H), 1.39 (tq,J1,J2=7.2Hz, 2H), 0.95 (t, J=7.2 Hz, 3H). GC-MS: m/z=375 (M+).

Provenance & Evidence