Bromine → 1-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 73959

Reaction equation

HRID 73959 reaction equation
[N:1]1([C:10](=[O:12])[CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br:13]Br>C(O)(=O)C>[Br:13][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[N:1]([C:10](=[O:12])[CH3:11])[CH2:2][CH2:3]2

Participants

4

Reactant 2

HCID 24408BromineHCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 7218471-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-oneYield 115.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-(2,3-dihydro-indol-1-yl)-ethanone (58.0 g, 0.36 mol) in acetic acid (3000 mL) was added Br2 (87.0 g, 0.54 mol) at 10° C. The mixture was stirred at room temperature for 4 h. The precipitate was collected via filtration to give crude 1-(5-bromo-2,3-dihydro-indol-1-yl)-ethanone (100 g, 96%), which was used directly in the next step.

Workup

  1. filtrationThe precipitate was collected via filtration

Sources & evidence

ORD record
ord-df565d59e78f441d895c727fcf848102
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Linked notes

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