Dimethylformamide → 3-Tert-butylbenzonitrile

HRID 2070986Notes

Reaction equation

HRID 2070986 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1)(=O)=O.[CH3:19][N:20](C=O)C>CCOCC.[C-]#N.[Zn+2].[C-]#N>[C:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:19]#[N:20])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 22261847HCID 22261847, compound

Product 1

HCID 1407313-Tert-butylbenzonitrileYield 75%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-tert-butylphenyl trifluoromethanesulfonate (1.5 g, 6.70 mmol) in DMF (10 mL), zinc cyanide (1.57 g, 13.40 mmol) was added. The reaction mixture was heated to 120° C. for 4 h. Then reaction mixture was cooled, diluted with ether (2500 mL) and washed twice with 2N ammonium hydroxide (50 mL). The ether solution was washed with brine (20 mL) and concentrated in vacuo to provide the crude mixture. The crude was then purified by column chromatography (5% EtOAc in hexanes) to afford 3-tert-butylbenzonitrile in 75% yield.

Workup

  1. customThen reaction mixture
  2. temperaturewas cooled
  3. washwashed twice with 2N ammonium hydroxide (50 mL)
  4. washThe ether solution was washed with brine (20 mL)
  5. concentrationconcentrated in vacuo
  6. customto provide the crude mixture
  7. customThe crude was then purified by column chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f60f70dd20d246ab967727e9ec83bb48
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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