Ethyl Acetate → 3-Fluoro-5-methoxy-4-nitrobenzonitrile

HRID 1880967Notes

Reaction equation

HRID 1880967 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1.[C:14]([Cu])#[N:15].C(OCC)(=O)C>CN(C=O)C>[F:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([O:12][CH3:13])[C:5]=1[N+:9]([O-:11])=[O:10])[C:14]#[N:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 579556485-Bromo-3-fluoro-2-nitroanisoleHCID 178418546HCID 178418546, compound

Product 1

HCID 579555403-Fluoro-5-methoxy-4-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-bromo-1-fluoro-3-methoxy-2-nitrobenzene (1.5 g, 6 mmol), and CuCN (698 mg, 7.8 mmol) in 10 mL of DMF was heated in a sealed tube at 160° C. overnight. It was then cooled down, diluted to ethyl acetate, washed by brine and water. The organic extract was dried and concentrated to a red solid (1 g, 85%) which was used for next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.01 (s, 3 H) 7.14 (s, 1 H) 7.17 (d, J=8 Hz, 1 H).

Workup

  1. temperatureIt was then cooled down
  2. washwashed by brine and water
  3. extractionThe organic extract
  4. customwas dried
  5. concentrationconcentrated to a red solid (1 g, 85%) which
  6. customwas used for next step without further purification

Sources & evidence

ORD record
ord-636a9c1d7e9346e5a7ce0efdee740d58
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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