Hydrochloric Acid → Methyl 4-(bromoacetyl)-7-methoxy-1H-indole-2-carboxylate

HRID 1762936Notes

Reaction equation

HRID 1762936 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[O:14][CH3:15])=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[Br:20][CH2:21][C:22](Br)=[O:23].Cl>ClCCl>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([C:22](=[O:23])[CH2:21][Br:20])[CH:10]=[CH:9][C:8]=2[O:14][CH3:15])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 10774603Methyl 7-methoxy-1H-indole-2-carboxylate

Product 1

HCID 13105653Methyl 4-(bromoacetyl)-7-methoxy-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A-2. A solution of 1.02 g of 7-methoxyindole--2carboxylic acid methyl ester in 25 ml of dichloromethane is combined with 2 g of aluminum chloride and 0.65 ml of bromoacetyl bromide and the mixture is heated for 3 hours under reflux. The reaction mixture is allowed to cool and poured into 100 ml of a mixture of equal parts of ice water and concentrated hydrochloric acid. The organic phase is separated, concentrated to dryness under vacuum, and recrystallization from acetonitrile yields 650 mg of 4-bromoacetyl-7-methoxyindole-2-carboxylic acid methyl ester, mp 197°-201° C.

Workup

  1. temperaturethe mixture is heated for 3 hours
  2. temperatureunder reflux
  3. temperatureto cool
  4. customThe organic phase is separated
  5. concentrationconcentrated to dryness under vacuum, and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-e25929d31f264d17bd7f1cb3a51b0a23
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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