Sodium Cyanide → (4-Chloro-3-methoxyphenyl)acetonitrile

HRID 17906Notes

Reaction equation

HRID 17906 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][CH3:11])[CH:4]=1.[C-:12]#[N:13].[Na+]>C(O)C>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:12]#[N:13])=[CH:4][C:5]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzene

Product 1

HCID 20460956(4-Chloro-3-methoxyphenyl)acetonitrileYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.29 mol) in C2H5OH (90%, 500 mL) was added NaCN (28.5 g, 0.58 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48%). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5.

Workup

  1. customEthanol was evaporated
  2. dissolutionthe residue was dissolved in H2O
  3. extractionThe mixture was extracted with ethyl acetate (300 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. custompurified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1)

Sources & evidence

ORD record
ord-8d1b0fffb0654d6eb2b8b05490eca8ea
Source dataset
uspto-grants-2010_06
Patent number
US07741321B2

Reaction notes

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