Carbazole → N-(3-Bromopropyl)carbazole

Temperature

30 °C

A 250-mL round-bottomed flask was charged with a solution of 9H-carbazole (5 g, 29.94 mmol, 1.00 equiv) in THF (200 mL). To this was added NaH (1.8 g, 75.00 mmol, 1.50 equiv) in small portions at and allowed to stir for 30 minutes. To the mixture was added 1,3-dibromopropane (18 g, 89.55 mmol, 3.00 equiv) at −10° C. and warmed up to 30° C. in an oil bath for 30 minutes. The reaction progress was monitored by TLC (EtOAc:PE=1:5). Upon completion, the reaction was then quenched by the addition of water (100 mL). The resulting mixture was extracted with ethyl acetate (3×50 mL). Combined organic layers were washed with brine (3×50 mL), dried over anhydrous sodium sulfate. Solids were filtered off and the mixture was concentrated on a rotary evaporator affording 9-(3-bromopropyl)-9H-carbazole as yellow solid (10 g).

1. customUpon completion, the reaction was then quenched by the addition of water (100 mL)
2. extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
3. washCombined organic layers were washed with brine (3×50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationSolids were filtered off
6. concentrationthe mixture was concentrated on a rotary evaporator

ORD record

ord-0d3118d0b72a4794af2b95963e3290fb

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080566B1