Ethyl Acetate → 2-Chloro-4-methylbenzonitrile

HRID 2233298Notes

Reaction equation

HRID 2233298 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[Cl:9].[Cu][C:11]#[N:12].C(OCC)(=O)C>CN(C)C=O>[Cl:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[C:11]#[N:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1387894-Bromo-3-chlorotolueneHCID 178418546HCID 178418546, compound

Product 1

HCID 3194752-Chloro-4-methylbenzonitrileYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

25.0 g 4-bromo-3-chlorotoluene and 21.8 g copper (I) cyanide were dissolved in 200 ml dimethylformamide and stirred at 150° C. for three hours. The cooled reaction mixture was diluted by addition of 300 ml ethyl acetate and washed three times with portions of 150 ml saturated NH4Cl solution. The precipitates were filtered off and the filtrate dried over MgSO4 and then reduced in vacuo to obtain 17.3 g 2-Chloro-4-methyl-benzonitrile. This material was used without purification in the next step.

Workup

  1. customThe cooled reaction mixture
  2. washwashed three times with portions of 150 ml saturated NH4Cl solution
  3. filtrationThe precipitates were filtered off
  4. dry with materialthe filtrate dried over MgSO4

Sources & evidence

ORD record
ord-d6dee5f1dc404904aaaf1432c2c9bfdf
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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