Potassium Cyanide → HCID 58691835, compound

HRID 2373701Notes

Reaction equation

HRID 2373701 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([Br:9])[C:6]=1[CH2:7]Br.[C-:10]#[N:11].[K+]>CCO.O>[Br:1][C:2]1[S:3][CH:4]=[C:5]([Br:9])[C:6]=1[CH2:7][C:10]#[N:11]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 58691834HCID 58691834, compound

Product 1

HCID 58691835HCID 58691835, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,4-dibromo-3-(bromomethyl)thiophene (1.00 g, 3.00 mmol) in EtOH (10 mL) was added a solution of potassium cyanide (0.29 g, 4.5 mmol) in H2O (0.5 mL). The mixture was heated to reflux overnight. The solvent was removed and the residue was partitioned between EtOAc and H2O. The EtOAc was dried (MgSO4) and the solvent removed. The residue was recrystalized from EtOH to yield (2,4-dibromothien-3-yl)acetonitrile (0.72 g, 86%). mp 75.5-77° C.; 1H NMR (500 MHz, DMSO-d6) δ: 3.94 (s, 2H), 7.94 (s, 1H). MS (EI) m/z 279/281/283 (M+.). Anal. Calcd for C6H3Br2NS: C, 25.65; H, 1.08; N, 4.99. Found: C, 26.04; H, 1.18; N, 4.86.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. customthe residue was partitioned between EtOAc and H2O
  5. dry with materialThe EtOAc was dried (MgSO4)
  6. customthe solvent removed
  7. customThe residue was recrystalized from EtOH

Sources & evidence

ORD record
ord-601d4c9f08d740b08807da7c60a08b21
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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