Dimethylformamide → 3-Methoxy-5-methylbenzonitrile

HRID 2194798Notes

Reaction equation

HRID 2194798 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[CH:3]=1.[CH3:11][N:12](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH3:10][O:9][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH3:8])[CH:5]=1)[C:11]#[N:12]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 106795541-Bromo-3-methoxy-5-methylbenzene

Product 1

HCID 219499033-Methoxy-5-methylbenzonitrileYield 83%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

In a 100 mL round bottom flask, 1-bromo-3-methoxy-5-methyl-benzene (2.17 g, 10.79 mmol), Zn(CN)2 (1.9 g, 16.19 mmol, 1.5 eq.) and Pd(PPh3)4 (1.24 g, 1.08 mmol, 0.1 eq.) was charged with DMF (20 mL). The reaction mixture was heated at 90° C. under Ar for 7 hours. Ethyl acetate was added, followed by washing with brine. The organic layer was concentrated and purified (silica gel, 0-50% EtOAC/hexane) to give a white solid (1.31 g, 83%). 1H NMR (300 MHz, CDCl3): δ 7.05 (s, 1H), 6.97 (s, 2H), 3.81 (s, 3H), 2.39 (s, 3H).

Workup

  1. washby washing with brine
  2. concentrationThe organic layer was concentrated
  3. custompurified (silica gel, 0-50% EtOAC/hexane)

Sources & evidence

ORD record
ord-0e9d719902e241899b1fc247c6c33709
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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