Water → 4-Bromo-2-fluoro-3-methylbenzonitrile

HRID 1967227Notes

Reaction equation

HRID 1967227 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[C:3]=1[CH3:10].O.[CH3:12][N:13](C=O)C>[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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]#[N:13])=[C:4]([F:9])[C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 59556994HCID 59556994, compound

Product 1

HCID 595569134-Bromo-2-fluoro-3-methylbenzonitrileYield 89%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a solution of 1-bromo-3-fluoro-4-iodo-2-methylbenzene (2.00 g) in DMF (15 mL) were added zinc cyanide (336 mg) and tetrakis(triphenylphosphine)palladium(0) (367 mg), and the mixture was stirred under an argon atmosphere at 100° C. for 5.5 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (yield: 1.21 g, 89%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b7e7c39cd3c74b1a9ed8723786c5ba0e
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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