Potassium Carbonate → Methyl 2-(3-phenyl-9H-carbazolyl)benzoate

HRID 1485582Notes

Reaction equation

HRID 1485582 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.[Cu]>[C:1]1([C:7]2[CH:8]=[C:9]([C:21]3[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=3[C:23]([O:25][CH3:26])=[O:24])[C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 134974733-Phenyl-9H-carbazole

Product 1

HCID 71008232Methyl 2-(3-phenyl-9H-carbazolyl)benzoate

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
1300 °C

Procedure

85 g (350 mmol) of 3-phenyl-9H-carbazole, 63 ml (262 mmol) of methyl 2-iodobenzoate, 20 g (315 mmol) of copper powder, 87 g (631 mmol) of potassium carbonate and 9.3 g (35 mmol) of 18-crown-6 are initially introduced in 1200 ml of DMF under a protective gas and heated at 1300° C. for 86 h. The mixture is subsequently evaporated and washed by stirring with hot heptane and purified by chromatography (heptane, dichloromethane 1:1). The product is washed by stirring with hot hexane, and the solid is isolated.

Workup

  1. customThe mixture is subsequently evaporated
  2. washwashed
  3. custompurified by chromatography (heptane, dichloromethane 1:1)
  4. washThe product is washed
  5. stirringby stirring with hot hexane
  6. customthe solid is isolated

Sources & evidence

ORD record
ord-d49562b7c5c24056bfdd4e167f847246
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

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