Acetic Anhydride → 1-Acetyl-4-bromo-1H-indole-3-carbaldehyde

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:11]=[O:12])=[CH:5][NH:6]2.[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[C:13]([N:6]1[C:7]2[C:3](=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=2)[C:4]([CH:11]=[O:12])=[CH:5]1)(=[O:15])[CH3:14]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 27631784-Bromo-1H-indole-3-carbaldehyde

Product 1

HCID 534157881-Acetyl-4-bromo-1H-indole-3-carbaldehydeYield 74%

Procedure

4-Bromo-1H-indole-3-carbaldehyde (4.0 g, 17.8 mmol) was stirred in acetic anhydride (20 mL) at reflux for 4 h. The reaction was cooled and concentrated in vacuo. Cold MeOH was added to precipitate a white solid, which was collected by filtration to give 3.5 g (74%) of 1-acetyl-4-bromo-1H-indole-3-carbaldehyde. MS (ES) [m+H] calc'd for C11H8BrNO2, 266, 268; found 266, 268.

Workup

temperatureat reflux for 4 h
temperatureThe reaction was cooled
concentrationconcentrated in vacuo
additionCold MeOH was added
customto precipitate a white solid, which
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-855426df7db447ce9db464b7678926c2
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119655B2

Reaction notes

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