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Potassium Cyanide → 209796-27-0

HRID 518132
Notes
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Reaction equation

HRID 518132 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7]Br.[C-:9]#[N:10].[K+]>C(O)C.O>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C:9]#[N:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 111186613-Bromo-2-(bromomethyl)thiophene

Product 1

HCID 18628861209796-27-0Yield 71.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Bromo-2-(bromomethyl)thiophene (7.1 g) and potassium cyanide (2.7 g) were dissolved in ethanol (93 mL) and water (17 mL), and the mixture was stirred at 50° C. for 2 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added water. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0−80/20) to give the title compound (4.0 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added water
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0−80/20)

Sources & evidence

ORD record
ord-19d445681f4d4d2fb3aba1665c7d96b0
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115144B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes