Sodium Chloride → Ethyl 7-(2-chloroethoxy)-1-methyl-4-trifluoromethyl-2-indolecarboxylate

HRID 565062Notes

Reaction equation

HRID 565062 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][Cl:10].[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:27]([F:30])([F:29])[F:28])=[C:16]2[C:20]=1[N:19]([CH3:21])[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17]2.[Cl-].[Na+]>CN(C)C=O.[I-].[K+]>[Cl:10][CH2:9][CH2:8][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:27]([F:30])([F:28])[F:29])=[C:16]2[C:20]=1[N:19]([CH3:21])[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17]2

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 78491-Bromo-2-Chloroethane2×HCID 11430Potassium Carbonate2×HCID 21194312Ethyl 7-hydroxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate

Product 1

HCID 21194253Ethyl 7-(2-chloroethoxy)-1-methyl-4-trifluoromethyl-2-indolecarboxylateYield 63.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

After 2.17 g (15.7 mmol) of potassium carbonate, 2.25 g (15.7 mmol) of 1-bromo-2-chloroethane and 0.05 g of potassium iodide were added to a solution of 3.00 g (10.4 mmol) of ethyl 7-hydroxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate in 30 ml of dimethylformamide, the mixture was stirred at room temperature for 3 hours. Subsequently, 1.45 g (10.4 mmol) of potassium carbonate and 0.69 g (5.2 mmol) of 1-bromo-2-chloroethane were further added thereto. The mixture was stirred at 50° C. for an hour. After cooling to room temperature, the reaction mixture was poured into saturated sodium chloride aqueous solution and then extracted with ethyl acetate. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2.31 g of ethyl 7-(2-chloroethoxy)-1-methyl-4-trifluoromethyl-2-indolecarboxylate.

Workup

  1. stirringThe mixture was stirred at 50° C. for an hour
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc9cd6431ebb40368a0f61dfc3aa6c56
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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