Dimethylformamide → 4-Carbazol-9-ylmethylbenzoic acid methyl ester

HRID 403645Notes

Reaction equation

HRID 403645 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.[H-].[Na+].CN(C)C=O.[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1>O>[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][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:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6854CarbazoleHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 668730724-Carbazol-9-ylmethylbenzoic acid methyl esterYield 20.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Carbazole (0.80 g, 4.80 mmol) and sodium hydride (NaH) (60% in mineral oil, 0.25 g, 6.2 mmol) were added to a flask, which was charged with argon. DMF (dimethylformamide) (12 mL) was added and the mixture was stirred at 60° C. for 1 hour (h), after which 4-bromomethyl benzoic acid methyl ester (1.16 g, 4.8 mmol) was added, and the mixture was stirred at 80° C. overnight. Water was added and the product was extracted with CH2Cl2 (dichloromethane), dried (Na2SO4, sodium sulfate) and concentrated. The product was purified by column chromatography to give 310 mg of compound 28 as a white solid.

Workup

  1. additionwhich was charged with argon
  2. stirringthe mixture was stirred at 80° C. overnight
  3. extractionthe product was extracted with CH2Cl2 (dichloromethane)
  4. dry with materialdried (Na2SO4, sodium sulfate)
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-c36c2d67a4ed49c8a260d452a962892e
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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