Water → 2-(Cyanomethyl)thiophene-3-carbonitrile
Reaction equation
Br[CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[C-:10]#[N:11].[Na+].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:10]([CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9])#[N:11]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
2-Bromomethyl-3-cyanothiophene (2.746 g) was dissolved in toluene (40 ml), followed by the addition of a solution of sodium cyanide (2.002 g)/water (15 ml), and the mixture was stirred at 80° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a pale yellow solid (823 mg, yield; 43%).
Workup
- washwashed with an aqueous solution of saturated sodium bicarbonate
- dry with materialdried (over MgSO4)
- customevaporated
- customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)
Sources & evidence
- ORD record
- ord-7c43bdfb337547ee812e8e288ae0532f
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06790844B2
Reaction notes
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