Aluminum(III) Chloride → 2-Benzyl-5,6-dibromo-2,3,3a,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalen-7-one

Participants

Reaction Conditions

Reaction Steps

A slurry of AlCl3 (2.38 g, 18 mmol) in CH2Cl2 (21 ml) was cooled to 0° C. under N2. Next, a solution of the product from step d) (3.0 g, 6 mmol) in CH2Cl2 (9 ml) was added dropwise over 5 minutes and the reaction mixture was stirred for an additional 45 minutes at 0° C. The reaction was poured into ice cold 2M NaOH (100 ml) and extracted with CH2Cl2 (2×100 ml). The organic layer was dried (MgSO4), evaporated, and purified by silica-gel chromatography using a gradient of 0-50% ethyl acetate in hexane to give the subtitle product (696 mg, 27%). 1H NMR (300 MHz, CDCl3, ppm) 2.39-2.49 (m, 2H); 2.92 (br d, J=9 Hz, 1H); 3.24 (br d, J=9 Hz, 1H); 3.34-3.40 (m, 1H); 3.54 (d, J=13 Hz, 1H); 3.60 (d, 13 Hz, 1H); 3.76-3.81 (m, 1H); 7.13-7.32 (m, 5H); MS calculated for C16H13Br2NOS+H 428, observed 426, 428, 430.

Provenance & Evidence