HCID 56965791, compound → HCID 69910668, compound

HRID 352354Notes

Reaction equation

HRID 352354 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([CH2:14][CH3:15])[CH:3]=1.[Cu](C#N)[C:17]#[N:18]>CN(C)C=O.O>[C:17]([C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([CH2:14][CH3:15])[CH:3]=1)#[N:18]

Participants

5

Reactant 2

HCID 56965791HCID 56965791, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 69910668HCID 69910668, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

7.5 g of methyl 4-bromo-2-ethyl-6-methylphenylacetate were dissolved in 140 ml of dimethylformamide, 5.5 g of copper cyanide were added, and the mixture was heated for 18 hours at 130° C., until the reaction was complete. The mixture was then cooled to room temperature and diluted with water, and the product was extracted repeatedly using tert-butyl methyl ether. The combined organic phases were dried over magnesium sulphate, concentrated and distilled. This gave 3.4 g (52% of theory) of methyl 4-cyano-2-ethyl-6-methylphenylacetate of a boiling point of 123-130° C. and a melting point of 65-72° C.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionthe product was extracted repeatedly using tert-butyl methyl ether
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-f2ec2eb7817b4f4984e9618b6be94e81
Source dataset
uspto-grants-2004_06
Patent number
US06746990B2

Reaction notes

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