Ethyl Acetate → HCID 57973980, compound

HRID 1875055Notes

Reaction equation

HRID 1875055 reaction equation
[F:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[CH2:18]C(O)=O.C(OCC)(=O)C>C(#N)C.[Cu-]=O>[C:9]1([O:8][C:7]2[C:6]([N+:15]([O-:17])=[O:16])=[CH:5][CH:4]=[C:3]([CH3:18])[C:2]=2[F:1])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68488923HCID 68488923, compound

Product 1

HCID 57973980HCID 57973980, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Copper(I) oxide (0.077 g, 0.536 mmol) was added to a solution of [2-fluoro-4-nitro-3-(phenyloxy)phenyl]acetic acid (1.560 g, 5.36 mmol) in acetonitrile (20 mL). The mixture was heated in a 90° C. oil bath for 1 h. The reaction mixture was cooled to RT and the solvent was evaporated. The residue was taken up in dichloromethane and filtered through Celite. Flash chromatography (ethyl acetate:hexanes) gave 2-fluoro-3-methyl-6-nitrophenyl phenyl ether (0.888 g, 63.7% yield) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.74 (dd, 1H), 7.27-7.36 (m, 2H), 7.18 (t, 1H), 7.09 (t, 1H), 6.92 (d, 2H), 2.38 (s, 3H). ES MS: m/z 246 (M−1).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe solvent was evaporated
  3. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-751b287b91244c5ba3d01fb9f178e154
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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