Ethanol → HCID 58613354, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the bromo intermediate D5 (1.20 g, 0.0023 moles), 4-chlorophenylboronic acid (0.55 g, 0.0034 moles), K2CO3 (2M solution, 15 ml), ethanol (15 ml) and toluene (50 ml) at room temperature was degassed by bubbling argon through the solution for 10 minutes. Pd(PPh3)4 (0.4 g, 0.000375 moles) was added and the mixture heated at 60° C. under argon for 4 hours. Upon cooling the mixture was partitioned between water and ethyl acetate. The aqueous phase was re-extracted with ethyl acetate (×3) and the combined organic phase washed with water, brine then dried over anhydrous MgSO4. The solution was evaporated to dryness then purified by chromatography over silica eluting, with hexane up to 50% EtOAc/hexane, affording the title compound D7 as a white foam (1.09 g, 86%). M-H 547. 1H NMR: δ CDCl3 1.47 (9H, s) 2.83(4H, m), 3.50 (4H, m), 3.66 (3H,s), 6.55 (1H, s), 6.96 (1H, s), 7.12 (1H, d), 7.33–7.50 (5H, m).

Provenance & Evidence