Ethanol → 2-Chloro-6-ethoxybenzonitrile

HRID 488429Notes

Reaction equation

HRID 488429 reaction equation
[CH3:1][C:2](C)([O-:4])C.[Na+].C(O)C.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14].C(Cl)(Cl)Cl>C1COCC1.O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([O:4][CH2:2][CH3:1])[C:12]=1[C:13]#[N:14]

Participants

7

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 695872-Chloro-6-fluorobenzonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 222709292-Chloro-6-ethoxybenzonitrileYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium t-butoxide (65 g, 0.642 mol) in THF (1 L), at room temperature under a dry nitrogen atmosphere, ethanol (250 mL, 5.35 mol) was added over a 10 minute period. To the resulting solution, 2-chloro-6-fluorobenzonitrile (100 g, 0.642 mol) was added in portions. The reaction mixture was stirred at room temperature for 30 minutes and then reduced to a volume of approximately 250 mL under reduced pressure. The resulting mixture was poured into chloroform and water and the layers separated. The organic layer was washed with water (twice) and brine, dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure to afford a light yellow solid. This material was recrystallized from hexanes to provide the 2-chloro-6-ethoxybenzonitrile, 135, (101 g, 87 % yield) as a white crystalline solid.

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with water (twice) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto afford a light yellow solid
  7. customThis material was recrystallized from hexanes

Sources & evidence

ORD record
ord-611ccf8a487e46e98079ae584d85714b
Source dataset
uspto-grants-2005_12
Patent number
US06972296B2

Reaction notes

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