Water → 4-Cyano-2-methylphenyl acetate

HRID 400591Notes

Reaction equation

HRID 400591 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[CH3:12])(=[O:3])[CH3:2].O.C[C:15]([N:17](C)C)=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:15]#[N:17])=[CH:7][C:6]=1[CH3:12])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 31374DimethylacetamideHCID 600267744-Bromo-2-methylphenyl acetate

Product 1

HCID 552203614-Cyano-2-methylphenyl acetateYield 99%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A solution of 4-bromo-2-methylphenyl acetate (6.9 g, 30 mol) in 75 mL of anhydrous dimethyl acetamide was treated with zinc cyanide (3 g, 25.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (4.5 g, 3.9 mmol). The reaction mixture was heated at 100° C. for 2 hours, cooled to room temperature, and treated with 300 mL of cold water. The resulting precipitate was filtered, washed with water, and air dried. Chromatography on SiO2 (100% dichloromethane) afforded 5.2 g of 4-cyano-2-methylphenyl acetate as a colorless oil (99% yield), which solidified on standing.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water, and air
  4. customdried

Sources & evidence

ORD record
ord-b34e50e40e044b50ac9b983d37558c2e
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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