Water → 2-(4-Bromo-2-methylphenyl)acetonitrile

HRID 603129Notes

Reaction equation

HRID 603129 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([CH3:10])[CH:3]=1.[C-:11]#[N:12].[Na+].O.C([O-])(O)=O.[Na+]>CN(C=O)C.CCCCCC.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:11]#[N:12])=[C:4]([CH3:10])[CH:3]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzene

Product 1

HCID 184142962-(4-Bromo-2-methylphenyl)acetonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
2.5 °C

Procedure

1-Bromo-4-(bromomethyl)-3-methylbenzene (13.2 g, 50.1 mmol) is dissolved in DMF (65 mL). The reaction mixture is cooled to 0-5° C. and NaCN (3.66 g, 74.6 mmol) is added follow by water (8 mL). The reaction is stirred overnight at room temperature and water (170 mL) is added followed by NaHCO3 sat. (130 mL) and hexane/Et2O (2:1) (150 mL). The organic phase is separated and the aqueous phase extracted with hexane/Et2O (2:1) (3×150 mL). The combined organic phases are washed with water (170 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide the expected product 2-(4-bromo-2-methylphenyl)acetonitrile (9.76 g, 93%) as an orange oil. 1H NMR (300 MHz, CHLOROFORM-D): δ 7.40-7.32 (2H, m), 7.23 (2H, d, J=8.2 Hz), 3.61 (2H, s), 2.32 (3H, s).

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous phase extracted with hexane/Et2O (2:1) (3×150 mL)
  3. washThe combined organic phases are washed with water (170 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-482d97157f1946ee8db1915ea869143a
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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