Potassium Cyanide → 3-(5-Bromothiophen-2-yl)-3-oxopropanenitrile

HRID 2267434Notes

Reaction equation

HRID 2267434 reaction equation
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([Br:10])=[CH:8][CH:9]=1)=[O:4].[C-:11]#[N:12].[K+]>C(O)C>[Br:10][C:7]1[S:6][C:5]([C:3](=[O:4])[CH2:2][C:11]#[N:12])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 19883982-Bromo-1-(5-bromothiophen-2-yl)ethan-1-one

Product 1

HCID 112876633-(5-Bromothiophen-2-yl)-3-oxopropanenitrileYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-1-(5-bromothiophen-2-yl)ethanone (5 g, 17.6 mmol) dissolved in ethanol (100 mL) was treated with an aqueous solution (10 mL) of potassium cyanide (6.19 g, 96.8 mmol) and stirred at ambient temperature overnight. The volatiles were removed in vacuo and crushed iced added to the residue which was acidified to pH 4 with acetic acid. The yellow precipitate that formed was collected by suction filtration and purified by flash chromatography on silica gel using a gradient of 10-30% of ethyl acetate in hexanes to yield a light gray solid (3 g).

Workup

  1. customThe volatiles were removed in vacuo
  2. customcrushed iced
  3. additionadded to the residue which
  4. customThe yellow precipitate that formed
  5. filtrationwas collected by suction filtration
  6. custompurified by flash chromatography on silica gel using a gradient of 10-30% of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4a93e3c5b7274e3fa0117503860c315b
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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