Potassium Iodide → 3,6-Diiodo-9-(4-methoxyphenyl)carbazole

HRID 1393884Notes

Reaction equation

HRID 1393884 reaction equation
[I:1]([O-])(=O)=O.[K+].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][CH:9]=1.[I-:27].[K+]>C(O)(=O)C>[I:27][C:23]1[CH:24]=[CH:25][C:26]2[N:14]([C:11]3[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=3)[C:15]3[C:20]([C:21]=2[CH:22]=1)=[CH:19][C:18]([I:1])=[CH:17][CH:16]=3

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 31108029-(4-Methoxyphenyl)carbazoleHCID 23665710Potassium Iodate

Product 1

HCID 583898553,6-Diiodo-9-(4-methoxyphenyl)carbazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium iodate (16.05 g, 75 mmol, obtained from Aldrich) was added in one portion to a stirred mixture of 9-(4-methoxyphenyl)carbazole (9.54 g, 34 mmol), potassium iodide (10.96 g, 66 mmol), and acetic acid (100 ml) at 80° C. The reaction mixture was stirred and heated for 1 hour. After the reaction was completed, the acetic acid was removed by distillation. The residue was dissolved in ethyl acetate and washed several times with an aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and dried. The yield of 3,6-diiodo-9-(4-methoxyphenyl)carbazole was 16.07 g (87.6%). The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 4.04 (s, 3H, OCH3), 7.24-7.63 (m, 6H, Ar), 8.35-8.40 (m, 4H, Ar). The mass spectrum of the product was characterized by the following ions (in m/z): 525 (M+).

Workup

  1. temperatureheated for 1 hour
  2. customthe acetic acid was removed by distillation
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed several times with an aqueous solution of sodium bicarbonate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-f635a731d740426cb6991944a2639e0c
Source dataset
uspto-grants-2008_03
Patent number
US07348116B2

Reaction notes

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