Acetyl chloride → Methyl 6-Bromo-1H-Indole-3-Carboxylate

HRID 1689809Notes

Reaction equation

HRID 1689809 reaction equation
[C:1](Cl)(=O)C.[Br:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:15]([OH:17])=[O:16])=[CH:11][NH:12]2)=[CH:8][CH:7]=1>CO>[CH3:1][O:16][C:15]([C:10]1[C:9]2[C:13](=[CH:14][C:6]([Br:5])=[CH:7][CH:8]=2)[NH:12][CH:11]=1)=[O:17]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 152848376-Bromo-1H-indole-3-carboxylic acid

Product 1

HCID 11499811Methyl 6-Bromo-1H-Indole-3-CarboxylateYield 72.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Acetyl chloride (29.43 g, 374 mmol) is added slowly at room temperature to a solution of 6-bromo-indole-3-carboxylic acid (45 g, 187.46 mmol) in 500 mL of methanol and the resulting solution is stirred at 65° C. overnight. The reaction is cooled to room temperature. A white precipitates appears when cooling. After stirring 2 h at room temperature, the solid is filtered off and dried under vacuum. 34.4 g (72%) of the title compound is obtained as a light brown solid. MS (m/e): 254 (M+1)

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. customA white precipitates
  3. temperaturecooling
  4. stirringAfter stirring 2 h at room temperature
  5. filtrationthe solid is filtered off
  6. customdried under vacuum

Sources & evidence

ORD record
ord-59ccc1a1124b447e9c1f8bb09a735dda
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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