Dimethylformamide → 2-Methoxy-6-methylbenzonitrile

HRID 1466070Notes

Reaction equation

HRID 1466070 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11]([Cu])#[N:12].CN(C=O)C>C(Cl)Cl>[CH3:10][O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[C:11]#[N:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 117902332-Bromo-3-methoxytolueneHCID 178418546HCID 178418546, compound

Product 1

HCID 5902262-Methoxy-6-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a flask containing a stir bar was added 2-bromo-1-methoxy-3-methylbenzene (7.5 g, 37 mmol), CuCN (6.7 g, 75 mmol) followed by addition of DMF (60 mL); the resulting mixture was then refluxed at 150° C. overnight. When the reaction was complete, as evidenced by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately. The solids were filtered, re-dissolved in DCM, absorbed into silica gel and loaded into column with Hexanes:EtOAc (1:1) to afford the title product.

Workup

  1. additionTo a flask containing a stir bar
  2. temperaturecooled to room temperature
  3. filtrationThe solids were filtered
  4. dissolutionre-dissolved in DCM
  5. customabsorbed into silica gel

Sources & evidence

ORD record
ord-e19fa2fd3d2f4c63a78c51bbbc15e8eb
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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