Chlorosuccinimide → 3-chloro-1H-indole-5-carbaldehyde

HRID 660023Notes

Reaction equation

HRID 660023 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:12]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 589040Indole-5-carboxaldehyde

Product 1

HCID 824092763-chloro-1H-indole-5-carbaldehydeYield 105.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1H-indole-5-carbaldehyde (0.50 g, 3.44 mmol) in DCM (25 mL) was added N-chlorosuccinimide (0.44 g, 3.27 mmol). After 4 h, the mixture was washed with water (50 mL) and the organic layer was dried and concentrated to obtain the crude residue (0.62 g), which was used without purification. 1H NMR (CDCl3): 10.04 (s, 1H), 8.17-8.15 (m, 1H), 7.79 (dd, J=8.6, 1.5 Hz, 1H), 7.46 (d, J=8.6 Hz, 1), 7.29-7.28 (m,1H).

Workup

  1. washthe mixture was washed with water (50 mL)
  2. customthe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-be7f6b26d82e49818279e3a6257a59ee
Source dataset
uspto-grants-2011_12
Patent number
US08084466B2

Reaction notes

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