Methyl iodide → 3-(Cyanomethyl)benzonitrile

HRID 489599Notes

Reaction equation

HRID 489599 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1.IC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl>[C:12]([C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH2:5][C:1]#[N:2])#[N:13]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 8929Sodium CyanideHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 5192803-(Cyanomethyl)benzonitrileYield 102%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9.8 g (200 mmole) of sodium cyanide and 1.61 g (5 mmole) of tetrabutylammonium bromide in 50 ml of water was added a solution of 19.61 g (100 mmole) of α-bromo-m-tolunitrile in 150 ml of dichloromethane. The mixture was stirred at room temperature for 24 hours. To this mixture was added 6.2 ml (100 mmole) of iodomethane. The mixture was stirred at room temperature for 3 hours. The layers were separated and the organic layer was dried over magnesium sulfate and was filtered. The filtrate was evaporated and the residue was triturated with petroleum ether and the insoluble material was collected to give 14.5 g of a white solid, mp-66-9° C.; 100% yield: 1H-NMR (300 MHz, CDCl3) δ (TMS) 3.80-3.90(s, 2H), 7.49-7.72(m, 4H).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationwas filtered
  5. customThe filtrate was evaporated
  6. customthe residue was triturated with petroleum ether
  7. customthe insoluble material was collected

Sources & evidence

ORD record
ord-ede4bd1a89314a6ea8808ca8b2383d24
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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