Dimethylformamide → 2-chloro-9-phenyl-9H-carbazole

HRID 1052921Notes

Reaction equation

HRID 1052921 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>[Cu].C(OCC)(=O)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 27523882-chloro-9H-carbazole

Product 1

HCID 681563502-chloro-9-phenyl-9H-carbazoleYield 57.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Next, a mixed solution of 17.7 g of 2-chloro-9H-carbazole, 22 g of iodobenzene, 20 g of a copper powder, 43 g of potassium carbonate and 200 ml of dimethylformamide was heated/stirred at 140° C. for 16 hours under a nitrogen flow. The solution was cooled to room temperature, 50 ml of ethyl acetate was added, and the mixture was filtered with Celite. To the resultant filtrate was added a saturated aqueous ammonium chloride solution, and the mixture was stirred for a while, and then extracted with ethyl acetate and hexane. The extract was dried over magnesium sulfate, and then evaporated. The concentrate was purified by silica gel column chromatography and vacuum-dried to obtain 14 g of 2-chloro-9-phenyl-9H-carbazole.

Workup

  1. filtrationthe mixture was filtered with Celite
  2. additionTo the resultant filtrate was added a saturated aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate and hexane
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated
  6. customThe concentrate was purified by silica gel column chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-f3895de9e4b241d7bcc9c8f535d8a843
Source dataset
uspto-grants-2016_07
Patent number
US09391288B2

Reaction notes

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