Carbazole → 9-(3-Bromophenyl)-9H-carbazole

Participants

Reaction Steps

Mix together 0.4 g Pd2DBA3 (DBA dibenzylideneacetone) and 0.4 g DPPF (DPPF 1,1′-bis(diphenylphosphino)ferrocene) and 4.3 g sodium t-butoxide and dissolve into 200 mL xylenes in glove box. Stir 15 mins then add 25 g of 3-iodo-bromobenzene. Stir 15 mins then add 5 g carbazole and the mix was brought to reflux. Reflux overnight using an air condensor in glove box. The solution immediately is dark purple/brown but on reaching ˜80 C. it is dark reddish brown and cloudy. After heating close to reflux overnight, the solution is dark brown and clear. Evaporated outside the glove box in rotovap and then dissolved in DCM and extracted (soxhlet) through a bed of silica and basic alumina (stacked in soxhlet) using DCM. Collect dark orange solution and evaporate to dryness. Leaves a dark orange oil. Wash with methanol and then dissolve into ether and reprecipitated with methanol—this product is slightly soluble in methanol.

Provenance & Evidence