Ethanol → 2-(3-Methyl-2-nitrophenyl)acetonitrile

HRID 2211881Notes

Reaction equation

HRID 2211881 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.CCO.[C-:16]#[N:17].[K+]>O>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][C:16]#[N:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 129324351-(Bromomethyl)-3-methyl-2-nitrobenzene

Product 1

HCID 137789352-(3-Methyl-2-nitrophenyl)acetonitrileYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A round bottomed flask was charged with 6.51 g (0.028 mol) of 3-methyl-2nitrobenzyl bromide, 120 mL 1:1 EtOH:H2O, and 5.5 g KCN (0.084 mol). The reaction solution was heated to 60° C. for 2 h. The reaction was cooled and the volatiles removed in vacuo. The resulting solid was dissolved in 150 mL water and extracted with 300 mL ethyl acetate. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated. This gave 4.63 g (92% yield) of the desired material as a slightly yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.45–7.41 (m, 2H), 7.33–7.31 (m,1H), 3.77 (s, 2H), 2.36 (s, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. customthe volatiles removed in vacuo
  3. dissolutionThe resulting solid was dissolved in 150 mL water
  4. extractionextracted with 300 mL ethyl acetate
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e0381ca114124483a1714177a859a152
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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