o-Bromocumene → isopropylbenzonitrile

HRID 1466436Notes

Reaction equation

HRID 1466436 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:10])[CH3:9].[C:11]([Cu])#[N:12]>CN(C=O)C>[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[N:12])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 23475o-BromocumeneHCID 178418546HCID 178418546, compound

Product 1

HCID 10920642isopropylbenzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a dry, N2 purged 100 mL round bottom flask attached with condenser was added 1-bromo-2-isopropylbenzene (10.0 g, 50.2 mmol), anhydrous DMF (26 mL), and CuCN (5.85 g, 653 mmol) The reaction slurry was stirred at reflux under N2 for 4 hrs prior to analysis by GCMS. The reaction mixture was cooled to room temperature and poured into an ice/aq NH4Cl solution. The resulting precipitates were removed by vacuum filtration through a Buchner funnel. The aqueous filtrate was extracted with EtOAc (150 mL×3). The combined organic phase was dried over Na2SO4, filtered and concentrated on the Rotavapor to afford 5.97 g (82% yield) of 2-isopropylbenzonitrile. The product was used in the next step without further purification. GCMS m/z=145 [M+].

Workup

  1. customTo a dry, N2 purged 100 mL round bottom flask
  2. customattached with condenser
  3. temperatureat reflux under N2 for 4 hrs
  4. customThe resulting precipitates
  5. customwere removed by vacuum filtration through a Buchner funnel
  6. extractionThe aqueous filtrate was extracted with EtOAc (150 mL×3)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated on the Rotavapor

Sources & evidence

ORD record
ord-4004a327901144e88be26f715657d6eb
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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