Methyl iodide → HCID 68289653, compound

HRID 878767Notes

Reaction equation

HRID 878767 reaction equation
[O-][CH2:2]C.[Na+].[Br:5][C:6]1[C:7]([CH2:14][C:15]#[N:16])=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].IC>C(O)C.O1CCCC1>[Br:5][C:6]1[C:7]([CH:14]([C:15]#[N:16])[CH3:2])=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 68289731HCID 68289731, compound

Product 1

HCID 68289653HCID 68289653, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium ethoxide (8.76 mL, 23.5 mmol, 21 wt % ethanol solution) in ethanol (10 mL) was cooled to 0° C. under argon atmosphere, and thereto was added dropwise a solution of 3-bromo-2-(cyanomethyl)benzonitrile (4.33 g, 19.6 mmol) and iodomethane (1.46 mL, 23.5 mmol) in tetrahydrofuran (10 mL) over 30 minutes, and then the mixture was stirred at room temperature for 6.5 hours. The mixture was concentrated under reduced pressure, and then the residue was neutralized by 2 mol/L hydrochloric acid, and extracted with ethyl acetate three times. The organic layer was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=10%→40%) to give 3-bromo-2-(1-cyanoethyl)benzonitrile (3.11 g, 67%) as a yellow viscous material.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate three times
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=10%→40%)

Sources & evidence

ORD record
ord-47a576466c564e65aa6ec2411365ace3
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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