1-Chloro-2-nitrobenzene → 4-(2-Nitrophenyl)indan-1-one

Participants

Reaction Conditions

Reaction Steps

Potash (8.1 g, 58.7 mmol) and Pd(PPh3)4 (1.7 g, 1.5 mmol) were added to a solution of compound 44 (7.51 g, 29.1 mmol) and 4-chloro-3-nitrobenzene (4.6 g, 29.1 mmol) in a mixture of dioxane (80 mL) and water (20 mL). The mixture obtained was heated under argon to 80° C., kept at this temperature for 16 h (TLC monitoring, eluent: hexane-ethyl acetate, 1:1), cooled, filtered through Celite, and evaporated. The resulting product was dissolved in CH2Cl2 and an insoluble residue was filtered off. The resulting product was evaporated with silica gel and purified on a short thick column (eluent: hexane-CH2Cl2100:0→0:100, CH2Cl2-ethyl acetate 100:0→50:50). Compound 45 (5.0 g) was isolated and used in the next step without purification.

Provenance & Evidence