Ethyl Acetate → HCID 21468951, compound

HRID 866262Notes

Reaction equation

HRID 866262 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)#[N:2].[Br:18]Br.C(OCC)(=O)C>CN(C=O)C.[Cl-].[Na+].O>[Br:18][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])[CH:10]=2)[NH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 21468934HCID 21468934, compound

Product 1

HCID 21468951HCID 21468951, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

5-(2-Cyanophenyl)indole (1.38 moles, 300 mg) was dissolved in DMF (1 ml). A solution of bromine (1.4 mmoles, 0.074 ml) in 0.5 ml DMF was added. The reaction was poured into ethyl acetate and brine. The organic phase was washed with water, dried over sodium sulfate, and concentrated. The intermediate was chromatographed over silica gel eluted with 50 % ether in hexane to yield 380 mg of 3-bromo-5-(2-cyanophenyl)indole (MS)

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe intermediate was chromatographed over silica gel
  5. washeluted with 50 % ether in hexane

Sources & evidence

ORD record
ord-2bce9221e1214abfa2ef7c698a7812d2
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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