Chlorosulfonyl isocyanate → 6-Bromo-1H-indole-3-carbonitrile

HRID 1027986Notes

Reaction equation

HRID 1027986 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.ClS([N:15]=[C:16]=O)(=O)=O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]#[N:15])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 6764936-Bromoindole

Product 1

HCID 114700676-Bromo-1H-indole-3-carbonitrileYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-bromo-1H-indole (41.36 g, 211.0 mmol) in DMF (150 mL) at −78° C. was added chlorosulfonyl isocyanate (20 mL, 225 mmol). After complete addition, the mixture was allowed to warm to room temperature and stirred for 2 hrs. The reaction mixture was poured into ice (500 mL) and stirred for 30 minutes. The precipitate was collected on a filter and dried in a vacuum oven to give 6-bromo-1H-indole-3-carbonitrile as a light-beige solid (46.73 g, 100%).

Workup

  1. additionAfter complete addition
  2. stirringstirred for 30 minutes
  3. customThe precipitate was collected on
  4. filtrationa filter
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-eadf67fb14f44d17b7dba449aee1e58d
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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