Carbazole → 9-(3-bromophenyl)-3,6-diphenyl-9H-Carbazole

Participants

Reaction Steps

Mix together 0.4 g Pd2DBA3 and 0.4 g DPPF 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 10 g carbazole and the mix brought to reflux. Reflux o/n. using an air condensor. 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 reprecipitate with methanol.

Provenance & Evidence