Ethyl Acetate → HCID 118045619, compound

HRID 596055Notes

Reaction equation

HRID 596055 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](I)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:13])[CH:3]=1.[C:14]([Cu])#[N:15].CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([F:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:10]([C:14]#[N:15])[CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 118045862HCID 118045862, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 118045619HCID 118045619, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Methyl 4-chloro-2-fluoro-6-iodobenzoate (1.99 g, 10.6 mmol) was dissolved in DMF (12 mL). CuCN (2.84 g, 31.7 mmol) was added and the suspension was heated under microwave at 110° C. for 18 min. EtOAc was added and the suspension was filtered through a piece of filter paper. The filtrate was washed three times with water. The aqueous layers were combined and extracted once with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated. The residue was purified on a silica gel column (heptane:EtOAc 1:0 to 9:1) to give the product as a colorless solid (505 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.56 (s, 1H), 7.40 (d, 1H, J=8 Hz), 4.00 (s, 3H); 13C NMR (100 MHz, CDCl3) δ ppm 161.78 (d, J=58 Hz), 159.44, 139.16 (d, J=11 Hz), 129.96, 121.99, 121.74, 115.48, 114.72, 53.04.

Workup

  1. filtrationthe suspension was filtered through a piece of filter paper
  2. washThe filtrate was washed three times with water
  3. extractionextracted once with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column (heptane:EtOAc 1:0 to 9:1)

Sources & evidence

ORD record
ord-a7c5ee4cf7654c6fae3eb5cdde90d392
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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