1-Bromo-4-iodobenzene → 2-(4-Bromophenyl)-1,3-dihydroisoindole

Participants

Reaction Conditions

Reaction Steps

palladium(II) acetate (0.112 g, 0.50 mmol) and XANTPHOS (0.288 g, 0.50 mmol) were added to a degassed solution of isoindoline (0.566 ml, 4.98 mmol), 1-bromo-4-iodobenzene (1.41 g, 4.98 mmol) and SODIUM TERT-BUTOXIDE (1.197 g, 12.46 mmol) in toluene (49.3 ml) under nitrogen. The resulting solution was stirred at 100 °C for 18 hours. The reaction mixture was allowed to cool to RT and was partitioned between EtOAc and H2O, filtered and the organic layer separated and dried over MgSO4, filtered and evaporated to dryness to give crude product. The crude product preabsorbed onto SiO2 and was purified by flash silica (40g, grace) chromatography, elution gradient 0 to 10% DCM in heptane. Pure fractions were evaporated to dryness to afford 2-(4-bromophenyl)isoindoline (0.660 g, 48.3 %) as an orange solid.

Provenance & Evidence