Potassium Cyanide → 2-(4-Bromo-3-methylphenyl)acetonitrile

HRID 603123Notes

Reaction equation

HRID 603123 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][C:3]=1[CH3:10].[C-:11]#[N:12].[K+]>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:11]#[N:12])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 118322651-Bromo-4-(bromomethyl)-2-methylbenzene

Product 1

HCID 184143092-(4-Bromo-3-methylphenyl)acetonitrileYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-Bromo-4-(bromomethyl)-2-methylbenzene (45 of crude from step b, 68.2 mmol) dissolved in CH2Cl2 (500 mL) is mixed and stirred with potassium cyanide (24 g, 364 mmol) and N-tetra(n-butyl)ammonium bromide (1.2 g, 3.64 mmol) in distilled water (500 mL). This reaction mixture is stirred vigorously for 6 h. The organic phase is separated, dried over MgSO4, filtered and concentrated. The resulting residue is purified on silica gel using a 0 to 30% gradient of ethyl acetate in heptane to provide the expected product 2-(4-bromo-3-methylphenyl)acetonitrile (12.4 g, 87% over two steps) as a clear yellow oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 2.41 (s, 3H) 3.68 (s, 2H) 7.01 (dd, J=8.50, 2.05 Hz, 1H) 7.21 (d, J=1.37 Hz, 1H) 7.53 (d, J=8.20 Hz, 1H)

Workup

  1. additionis mixed
  2. customThe organic phase is separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue is purified on silica gel using a 0 to 30% gradient of ethyl acetate in heptane

Sources & evidence

ORD record
ord-1714043a8bb54aa6b6d8419239f40b29
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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