Dichloromethane → ethyl 4-(7-bromo-1H-indol-3-yl)-4-oxobutanoate

HRID 12616Notes

Reaction equation

HRID 12616 reaction equation
ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:9]([O:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)[CH3:10].[Br:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:28]=1[NH:27][CH:26]=[CH:25]2>C(OCC)(=O)C>[Br:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:28]=1[NH:27][CH:26]=[C:25]2[C:15](=[O:17])[CH2:14][CH2:13][C:12]([O:11][CH2:9][CH3:10])=[O:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 27570207-BromoindoleHCID 6451240Aluminum(III) ChlorideHCID 77519041Succinic acid monoethyl ester monochloride

Product 1

HCID 66738889ethyl 4-(7-bromo-1H-indol-3-yl)-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane (50 mL) solution of aluminum chloride (6.80 g), succinic acid monoethyl ester chloride (8.39 g) was added under ice cooling and the mixture was stirred for 30 minutes. To the mixture, 7-bromoindole (5.0 g) was added, followed by stirring at room temperature for 5 hours. To the reaction mixture, ice water and ethyl acetate were added, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was washed with diisopropyl ether to obtain the titled compound having the following physical properties (6.04 g).

Workup

  1. stirringby stirring at room temperature for 5 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed in turn with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-e993f9013eb04841a817eda50d228980
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Reaction notes

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