Ethyl Acetate → 3-Bromo-1H-indole-4-carbonitrile

HRID 80187Notes

Reaction equation

HRID 80187 reaction equation
[Br:1]Br.[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]#[N:13])[C:6]=2[CH:5]=[CH:4]1.C(OC(=O)C)C.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.CCCCCC>[Br:1][C:5]1[C:6]2[C:7]([C:12]#[N:13])=[CH:8][CH:9]=[CH:10][C:11]=2[NH:3][CH:4]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 656671Sodium PyrosulfiteHCID 38176024-Cyanoindole

Product 1

HCID 533932493-Bromo-1H-indole-4-carbonitrileYield 78.41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

Bromine in DMF (0.796 g, 4.975 mmol) was added to a stirred solution of 1H-indole-4-carbonitrile (700 mg, 4.9295 mmol) in DMF (15 mL) at room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was poured into ice water containing 0.5% ammonia and 0.5% sodium metabisulphite. The precipitate was collected, washed with cold water and dried to afford 850 mg of 3-Bromo-1H-indole-4-carbonitrile (78.41% yield).

Workup

  1. customThe precipitate was collected
  2. washwashed with cold water
  3. customdried

Sources & evidence

ORD record
ord-960275e7b31c4f1586aa012566cabc4e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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