Carbazole → 3-Bromocarbazole

HRID 1516996Notes

Reaction equation

HRID 1516996 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH:9]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[Br:8][C:11]1[CH:10]=[CH:9][C:21]2[NH:20][C:19]3[C:14]([C:13]=2[CH:12]=1)=[CH:15][CH:16]=[CH:17][CH:18]=3

Participants

4

Reactant 2

HCID 6854CarbazoleHCID 67184N-bromobutanimide

Product 1

HCID 2524463-BromocarbazoleYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (12.77 g, 71.8 mmol) in DMF was added to 9H-carbazole (12 g, 71.8 mmol) in 200 mL at 0° C. dropwise. The reaction was monitored by HPLC. After 2 h, HPLC indicated 76% of desired product and 6% of dibrominated compound. The reaction was quenched by adding 500 mL of ice water. The internal temperature was controlled to be lower than 10° C. The precipitate formed was collected by filtration. The solid was stirred in 400 mL of warm methanol. (˜40° C.). The solid was collected by filtration. The solid was dissolved in 150 mL of DCM. 200 mL of methanol was added. The DCM was boiled off. The solvent level was down to 150 mL. The slurry was stirred at room temperature overnight. The solid was collected by filtration. 9 g (51% yield) of solid was collected.

Sources & evidence

ORD record
ord-f6f87fa07ae848bcaa43783fdb66cca5
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

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