Sodium Cyanide → HCID 68505218, compound

HRID 1176315Notes

Reaction equation

HRID 1176315 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[C-:16]#[N:17].[Na+]>CS(C)=O>[C:16]([CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:17]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 68501144HCID 68501144, compound

Product 1

HCID 68505218HCID 68505218, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 11.92 g of methyl 7-bromomethylbenzofuran-2-carboxylate and 5.57 g of sodium cyanide in 150 ml of dimethyl sulphoxide is stirred at room temperature over 1 hour. The reaction mixture is poured onto water and extracted with ethyl acetate (3×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.23 (dichloromethane); Rt=3.86.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phases are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b469063e6d12449ea471970d0d5d918a
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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