Carbazole → 9-(4-Methoxyphenyl)carbazole

HRID 1393883Notes

Reaction equation

HRID 1393883 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.[Cu]>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 696764-Iodoanisole

Product 1

HCID 31108029-(4-Methoxyphenyl)carbazole

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 9H-carbazole (5.51 g, 33 mmol, available from Aldrich, Milwaukee, Wis.), 4-iodoanisole (10 g, 43 mmol, available from Aldrich), powdered potassium carbonate (36.43 g, 264 mmol), copper powder (8.38 g, 132 mmol) and 18-crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane, 0.56 g, 2.1 mmol, obtained from Aldrich) was refluxed in o-dichlorobenzene (30 ml, obtained from Aldrich) under nitrogen for 24 hours. The copper and inorganic salts were filtered. The solvent was removed by distillation. The product, 9-(4-methoxyphenyl)carbazole, was recrystallized, washed with methanol, filtered, and dried. The yield was 8.432 g (93.7%). The 1H-NMR spectrum (300 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, 8H, Ar.), 8.35-8.40 (m, 4H, Ar.). The 13C-NMR spectrum (75.4 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 55.95 (OCH3), 110.07, 115.44, 120.03, 120.68, 123.53, 126.25, 128.90, 130.65, 141.78, 159.26 (all Ar). The infrared absorption spectrum of the product was characterized by the following the following absorption frequencies (KBr windows, in cm−1): 3040 (C—H Ar), 2900 (C—H Alk), 1250 (C—O—C). The mass spectrum of the product was characterized by the following ions (in m/z): 274 (M+).

Workup

  1. filtrationThe copper and inorganic salts were filtered
  2. customThe solvent was removed by distillation
  3. customThe product, 9-(4-methoxyphenyl)carbazole, was recrystallized
  4. washwashed with methanol
  5. filtrationfiltered
  6. customdried
  7. customThe infrared absorption spectrum of the product
  8. customthe following absorption frequencies (KBr windows, in cm−1)

Sources & evidence

ORD record
ord-7c6c53e421fc4fcaaacfeeb4de3fceb3
Source dataset
uspto-grants-2008_03
Patent number
US07348116B2

Reaction notes

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